JP7202024B2 - Novel isoxazole compound or salt thereof - Google Patents

Description

The present invention relates to novel isoxazole compounds or salts.

In recent years, the use of some insecticides, acaricides or nematicides has been restricted due to environmental pollution and the gradual accumulation of pesticide residues in the environment.

In recent years, long-term use of acaricides has resulted in the emergence of mites resistant to acaricides, making it difficult to achieve control using existing acaricides. Therefore, there is an urgent need to develop novel miticides or nematicides that are thought to have different effects from commercially available miticides or nematicides.

For example, Patent Documents WO 2002/018352 and WO 97/046530 (Patent Documents 1 and 2) describe isoxazole derivatives substituted with a phenyl group. The 3-position of the phenyl group in this isoxazole derivative is limited to an alkylsulfonyl group. No uses other than herbicides are disclosed in these patents.

Agricultural and Biological Chemistry published in 1986 [50 (10), 2591 (1986)] (Non-Patent Document 1) describes a plant growth regulator containing an isoxazole derivative substituted with a 3-methylthio group. However, this isoxazole derivative is not described as a pest control agent for agricultural and horticultural purposes.

［式中、Ｒ^１は、アルキル、アルケニル又はシクロアルキルを表す。Ａは、ハロゲン、アルキル、アルケニル、アルキニル、シクロアルキル、（ヒドロキシイミノ）メチル、（アルコキシイミノ）メチル、ヘテロアリール又はシアノを表す。Ｘは、ハロゲンを表す。ｍは０～３の整数である。ｎは０～１の整数である。Ｑは、ヘテロアリール等を表す。］
で表される化合物が開示されている。 Japanese Patent Application Laid-Open No. 2008-308448, which is a patent document, describes the following formula (II):

[wherein R ¹ represents alkyl, alkenyl or cycloalkyl; A represents halogen, alkyl, alkenyl, alkynyl, cycloalkyl, (hydroxyimino)methyl, (alkoxyimino)methyl, heteroaryl or cyano. X represents halogen. m is an integer from 0 to 3; n is an integer from 0 to 1; Q represents heteroaryl and the like. ]
A compound represented by is disclosed.

［式中、Ｚ^１及びＺ^２は、水素、ハロゲン、ニトロ、シアノ、置換又は無置換のアミノ、置換又は無置換のアルキル、置換又は無置換のアルコキシ、置換又は無置換のアルキルチオ等を表す。Ｒ^１、Ａ、Ｘ、ｍ及びｎは、上記定義されたとおりである。］
で表される化合物も開示されている。 The above-mentioned publication describes the following formula (III):

[In the formula, Z ¹ and Z ² represent hydrogen, halogen, nitro, cyano, substituted or unsubstituted amino, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylthio, and the like. R ¹ , A, X, m and n are as defined above. ]
A compound represented by is also disclosed.

This publication further discloses that the compounds represented by formulas (II) and (III) exhibit acaricidal and nematicidal activity.

However, the examples of the same publication only show that the compounds represented by formulas (II) and (III) exhibit acaricidal activity against two-spotted spider mites and citrus spider mites at a high concentration of 300 ppm. No effect on mite eggs was described.

In addition, among the compounds of the formula (III), those of the formula (III) in which n is 0 are particularly preferred, but their acaricidal and ovicidal activity are quite unsatisfactory.

WO2002/018352 WO 97/046530 Japanese Patent Application Laid-Open No. 2008-308448

Agricultural and Biological Chemistry, 50(10), 2591 (1986)

INDUSTRIAL APPLICABILITY The present invention provides an isoxazole compound or a salt thereof having excellent effects not only on adult mites but also on eggs or eggs.

The present invention also provides an isoxazole compound or a salt thereof that has an excellent control effect on mites and/or eggs even when used at a low concentration.

Furthermore, the present invention provides an isoxazole compound or a salt thereof that has a high control effect on mites and/or eggs that have acquired resistance to existing acaricides.

The present invention also provides acaricides, ovicides and nematicides containing the isoxazole compounds or salts thereof.

Specifically, as a result of extensive studies, the present inventors have found that a compound represented by the following general formula (I) or a salt thereof exhibits excellent acaricidal activity at low concentrations. At the same time, the compounds of formula (I) also exhibit ovicidal activity against mites for agricultural and horticultural use, in particular those represented by two-spotted spider mites, citrus spider mites and Kanzawa spider mites. Furthermore, the compound represented by formula (I) was found to have extremely excellent nematicidal activity at low concentrations against nematodes such as root-knot nematode and Negusare nematode. the invention is complete.

Therefore, the present invention relates to a novel isoxazole compound represented by the following formula (I) or a salt thereof.

More specifically, the present invention includes the following embodiments.

［式中、Ｒは、Ｃ_１－６アルキル又はＣ_１－４ハロアルキルを表す。
Ａ^１及びＡ^２は、同一又は異なり、それぞれハロゲン又はＣ_１－６アルキルである。
Ｂ^１は、水素、ハロゲン又はＣ_１－６アルキルを表す。
Ｂ^２は、Ｃ_１－６アルキル、Ｃ_１－４ハロアルキル又は置換若しくは無置換のアリールＣ_１－４ハロアルキルを表す。
ｎは０～２の整数を表す。］
で表されるイソオキサゾール化合物又はその塩。 Item 1:
Formula (I):

[In the formula, R represents C _1-6 alkyl or C _1-4 haloalkyl.
A ¹ and A ² are the same or different and each is halogen or C _1-6 alkyl.
B ¹ represents hydrogen, halogen or C _1-6 alkyl.
B ² represents C _1-6 alkyl, C _1-4 haloalkyl or substituted or unsubstituted aryl C _1-4 haloalkyl.
n represents an integer of 0 to 2; ]
Isoxazole compound represented by or a salt thereof.

Item 2:
Item 2. The isoxazole compound or a salt thereof according to Item 1, wherein R is normal-propyl or 2,2,2-trifluoroethyl.

Item 3:
Item 3. The isoxazole compound or its salt according to Item ¹ or 2, wherein A1 is fluorine, chlorine or methyl.

Item 4:
Item 4. The isoxazole compound or its salt according to any one of Items 1 to 3, wherein A ² is fluorine, chlorine or methyl.

Item 5:
Item 5. The isoxazole compound or salt thereof according to any one of Items 1 to 4, wherein B ¹ is hydrogen or methyl.

Item 6:
Item 6. The isoxazole compound or salt thereof according to any one of Items ¹ to 5, wherein B2 is difluoromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, heptafluoropropyl or difluoro(phenyl)methyl.

Item 7:
Item 7. The isoxazole compound or a salt thereof according to any one of items 1 to 6, wherein n is an integer of 0 or 1.

Item 8:
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(heptafluoropropyl)isoxazole;
5-(difluoromethyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
5-(chlorodifluoromethyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)isoxazole;
5-(difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole;
5-(difluoromethyl)-3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
5-(difluoromethyl)-3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)isoxazole;
5-(chlorodifluoromethyl)-3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
5-(chlorodifluoromethyl)-3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoro(phenyl)methyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoro(phenyl)methyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoromethyl)isoxazole; and 3-(2-chloro-4-methyl Item 2. The isoxazole compound or a salt thereof according to Item 1, which is selected from the group consisting of -5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoromethyl)isoxazole.

Item 9:
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(heptafluoropropyl)isoxazole;
5-(difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoromethyl)isoxazole; and 3-(2-chloro-4-methyl Item 2. The isoxazole compound or a salt thereof according to Item 1, which is selected from the group consisting of -5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoromethyl)isoxazole.

Item 10:
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
5-(chlorodifluoromethyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)isoxazole;
5-(difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoromethyl)isoxazole; and 3-(2-chloro-4-methyl Item 2. The isoxazole compound or a salt thereof according to Item 1, which is selected from the group consisting of -5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoromethyl)isoxazole.

Item 11:
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
5-(difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoromethyl)isoxazole; and 3-(2-chloro-4-methyl Item 2. The isoxazole compound or a salt thereof according to Item 1, which is selected from the group consisting of -5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoromethyl)isoxazole.

Item 12:
Item 12. A pest control agent comprising the isoxazole compound or its salt according to any one of Items 1 to 11 as an active ingredient.

Section 12-1:
Item 12. Acaricide comprising the isoxazole compound or its salt according to any one of Items 1 to 11 as an active ingredient.

Section 12-2:
Item 12. A nematicide comprising the isoxazole compound or its salt according to any one of Items 1 to 11 as an active ingredient.

Item 13:
An agricultural composition comprising the isoxazole compound or salt thereof according to any one of Items 1 to 11.

Item 14:
A composition for controlling pests, comprising the isoxazole compound or salt thereof according to any one of Items 1 to 11.

Item 15:
Acaricidal composition comprising the isoxazole compound or salt thereof according to any one of Items 1 to 11.

Item 16:
An ovicidal composition comprising the isoxazole compound or salt thereof according to any one of Items 1 to 11.

Item 17:
Item 12. A nematicidal composition comprising the isoxazole compound or its salt according to any one of items 1 to 11.

Item 18:
A composition for controlling mites, comprising the isoxazole compound or salt thereof according to any one of Items 1 to 11.

Item 19:
A composition for controlling eggs or eggs, comprising the isoxazole compound or salt thereof according to any one of Items 1 to 11.

Item 20:
A composition for controlling nematodes, comprising the isoxazole compound or salt thereof according to any one of Items 1 to 11.

Item 21:
A composition for use in controlling mites, comprising the isoxazole compound or salt thereof according to any one of Items 1 to 11.

Item 22:
A composition for use in controlling eggs or eggs, comprising the isoxazole compound or salt thereof according to any one of Items 1 to 11.

Item 23:
A composition for use in controlling nematodes, comprising the isoxazole compound or salt thereof according to any one of Items 1 to 11.

Item 24:
Item 12. A method of using the isoxazole compound or a salt thereof according to any one of Items 1 to 11 for controlling insect pests.

Section 24-1:
Item 12. A method for controlling mites, using the isoxazole compound or a salt thereof according to any one of items 1 to 11.

Section 24-2:
Item 12. A method of using the isoxazole compound or a salt thereof according to any one of Items 1 to 11 for controlling nematodes.

Item 25:
Item 12. A method for controlling pests, which comprises applying the isoxazole compound or its salt according to any one of Items 1 to 11 to a plant or its vicinity or to the soil in which the plant is cultivated.

Item 25-1:
Item 12. A method for controlling mites, which comprises applying the isoxazole compound or its salt according to any one of items 1 to 11 to a plant or its vicinity or to the soil in which the plant is cultivated.

Item 25-2:
Item 12. A method for controlling nematodes, which comprises applying the isoxazole compound or its salt according to any one of items 1 to 11 to a plant or its vicinity or to the soil in which the plant is cultivated.

Item 26:
A method for controlling pests, which comprises applying an effective amount of the isoxazole compound or salt thereof according to any one of Items 1 to 11 to pests, habitats of pests, or places where pests are expected to inhabit. .

Section 26-1:
12. A method for controlling ticks, which comprises applying an effective amount of the isoxazole compound or salt thereof according to any one of Items 1 to 11 to ticks, places where ticks live, or places where they are expected to live. .

Item 26-2:
Controlling nematodes, including applying an effective amount of the isoxazole compound or salt thereof according to any one of items 1 to 11 to nematodes, nematode habitats or locations where nematodes are expected to inhabit. way for.

Item 27:
Item 12. A method for killing mites, comprising applying the isoxazole compound or salt thereof according to any one of Items 1 to 11 to a plant or its vicinity or to the soil in which the plant is cultivated.

Item 28:
A method for killing mites, comprising applying an effective amount of the isoxazole compound or salt thereof according to any one of claims 1 to 11 to mites, mites' habitats or expected habitats. .

Item 29:
A method for killing eggs comprising applying the isoxazole compound or salt thereof according to any one of Items 1 to 11 to a plant or its vicinity or to the soil in which the plant is cultivated.

Item 30:
12. A method for killing eggs comprising applying an effective amount of an isoxazole compound or salt thereof according to any one of claims 1 to 11 to the eggs or locus where egg laying is expected.

Item 31:
Item 12. A method for killing nematodes, comprising applying the isoxazole compound or salt thereof according to any one of items 1 to 11 to a plant or its vicinity or to the soil in which the plant is cultivated.

Item 32:
Nematodes, including applying an effective amount of the isoxazole compound or salt thereof according to any one of Items 1 to 11 to nematodes, nematode habitats, or nematode habitats. way to kill.

Item 33:
Use of the isoxazole compound or salt thereof according to any one of claims 1 to 11 as an acaricide.

Item 34:
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(heptafluoropropyl)isoxazole;
5-(difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoromethyl)isoxazole; and 3-(2-chloro-4-methyl - Use of an isoxazole compound or a salt thereof selected from the group consisting of 5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoromethyl)isoxazole as an acaricide.

Item 35:
Use of the isoxazole compound or a salt thereof according to any one of Items 1 to 11 as an ovicide.

Item 36:
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
5-(chlorodifluoromethyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)isoxazole;
5-(difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoromethyl)isoxazole; and 3-(2-chloro-4-methyl - Use of an isoxazole compound or a salt thereof selected from the group consisting of 5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoromethyl)isoxazole as an ovicide.

Item 37:
Use of the isoxazole compound or salt thereof according to any one of Items 1 to 11 as a nematicide.

Item 38:
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(perfluoroethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfonyl)phenyl)-5-(perfluoropropyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(perfluorobutyl)isoxazole;
5-(difluoromethyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
5-(difluoromethyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)isoxazole;
5-(chlorodifluoromethyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)isoxazole;
5-(difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
5-(difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)sulfonyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2,4-difluoro-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2,4-dichloro-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5-(trifluoromethyl)isoxazole;
3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole;
5-(difluoro(phenyl)methyl)-3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole;
5-(difluoromethyl)-3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
5-(chlorodifluoromethyl)-3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole;
5-(chlorodifluoromethyl)-3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)isoxazole;
3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoromethyl)isoxazole; and 3-(2-chloro-4-methyl - Use of an isoxazole compound or a salt thereof selected from the group consisting of 5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoromethyl)isoxazole as a nematicide.

It is contemplated that one or more of the aforementioned features may be provided in combination with one or more of the aforementioned features in addition to the combinations explicitly shown. Further embodiments and advantages of the present invention will be appreciated by those skilled in the art upon reading and understanding the following detailed description as appropriate.

Advantageous Effects of the Invention According to the present invention, it is possible to provide an isoxazole compound or a salt thereof that has an excellent control effect on insect pests.

In particular, according to the present invention, it is possible to provide an isoxazole compound or a salt thereof, and an acaricide containing these compounds, which have excellent effects not only on adult mites but also on eggs even at low concentrations.

Furthermore, according to the present invention, it is possible to provide an isoxazole compound or a salt thereof having a high control effect against mites that have acquired resistance to existing acaricides, and an acaricide containing these compounds.

In addition, the isoxazole compound or salt thereof of the present invention has an excellent control effect on nematodes, and nematicides containing these compounds can be provided.

Description of Embodiments Hereinafter, the present invention will be described in more detail with reference to examples, but the technical scope of the present invention is not limited to these examples. Throughout the specification, singular expressions should be understood to include plural forms of the concept unless otherwise indicated. Thus, articles in the singular (eg, in the English language, “a,” “an,” “the,” etc.) should also be understood to include plural forms of the concept unless otherwise indicated. Further, the terms used herein should be understood to have the meanings commonly used in the art unless otherwise specified. Thus, unless defined otherwise, all terms and scientific and technical terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, the present specification (including definitions) will control.

［式中、Ｒ、Ａ^１、Ａ^２、Ｂ^１、Ｂ^２及びｎは、上記定義されたとおりである。］
で表されるイソオキサゾール化合物又はその塩を提供する。 Isoxazole compound or salt thereof The present invention provides a compound of formula (I):

[wherein R, A ¹ , A ² , B ¹ , B ² and n are as defined above. ]
To provide an isoxazole compound represented by or a salt thereof.

Specific examples of each group used in the present specification are shown below.

In this description, the term "unsubstituted" means that the base group is the only constituent group. In addition, unless otherwise specified, a group is meant to be "unsubstituted" when the group is not described as "substituted" and is described using the name of the base group. have.

The term "substituted," on the other hand, means that any hydrogen atom of the base group has been replaced with the same or different group as the base group. A "substituted" group may be substituted with one substituent or two or more substituents. Two or more substituents may be the same or different.

A "substituent" is not particularly limited as long as it is chemically acceptable and the effects of the present invention are exhibited.

Examples of "substituents" include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom and the like; C _1-6 alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, s -butyl, isobutyl, t-butyl, n-pentyl, n-hexyl etc.; C _3-8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl etc.; C _2-6 alkenyl such as vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4- Pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl etc.; C _3-8 cycloalkenyl, such as 2- cyclopropenyl, 2-cyclopentenyl, 3-cyclohexenyl, 4- _cyclooctenyl , etc.; methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 2-methyl-3-pentynyl, 1-hexynyl, 1,1-dimethyl-2-butynyl and the like; C _1-6 alkoxy such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, s-butoxy, isobutoxy, t-butoxy and the like; C _2-6 alkenyl oxy, such as vinyloxy, allyloxy, propenyloxy, butenyloxy, etc.; C _2-6 alkynyloxy, such as ethynyloxy, propargyloxy, etc.; C _6-10 aryl, such as phenyl, naphthyl, etc.; C _6-10 aryloxy, For example, phenoxy, 1-naphthoxy, etc.; C _7-11 aralkyl, such as benzyl, phenethyl, etc.; C _7-11 aralkyloxy, such as benzyloxy, phenethyloxy, etc.; C _1-7 acyl, such as formyl, acetyl, propionyl, benzoyl, cyclohexylcarbonyl etc.; _1-7 acyloxy such as formyloxy, acetyloxy, propionyloxy, benzoyloxy, cyclohexylcarbonyloxy etc.; C _1-6 alkoxy carbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, t-butoxycarbonyl, etc.; carboxyl; hydroxy; oxo; C _1-6 haloalkyl such as chloromethyl, chloroethyl, tri fluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl, perfluoro-n-pentyl and the like; C _2-6 haloalkenyls such as 2-chloro-1-propenyl, 2-fluoro- 1-butenyl and the like; C _2-6 haloalkynyl, for example 4,4-dichloro-1-butynyl, 4-fluoro-1-pentynyl, 5-bromo-2-pentynyl and the like; C _1-6 haloalkoxy, for example 2-chloro-n-propoxy, 2,3-dichlorobutoxy and the like; C _2-6 haloalkenyloxy, such as 2-chloropropenyloxy, 3-bromobutenyloxy and the like; C _6-10 haloaryl, such as 4- chlorophenyl, 4-fluorophenyl, 2,4-dichlorophenyl and the like; C _6-10 haloaryloxy, such as 4-fluorophenyloxy, 4-chloro-1-naphthoxy and the like; halogen-substituted C _1-7 acyl, such as , chloroacetyl, trifluoroacetyl, trichloroacetyl, 4- _{chlorobenzoyl} , etc.; cyano; _isocyano ; nitro; isocyanato; ₁₀ arylamino, such as anilino, naphthylamino, etc.; C _7-11 aralkylamino, such as benzylamino, phenylethylamino, etc.; C _1-7 acylamino, such as formylamino, acetylamino, propanoylamino, butyrylamino, isopropyl carbonylamino, benzoylamino, etc.; C _1-6 alkoxycarbonylamino, such as methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, isopropoxycarbonylamino, etc.; unsubstituted or substituted aminocarbonyl, such as aminocarbonyl, dimethyl aminocarbonyl, phenylaminocarbonyl, N-phenyl-N-methylaminocarbonyl, etc.; imino-substituted C _1-6 alkyl, such as iminomethyl, (1-imino)-ethyl, (1-imino)-n-propyl, etc.; hydroxy imino-substituted C _1-6 alkyl, such as hydroxyiminomethyl, (1-hydroxyimino)ethyl, (1-hydroxyimino)propyl, methoxyiminomethyl, (1-methoxyimino)ethyl, etc.; mercapto; isothiocyanato; thiocyanato; C _1-6 alkylthio, such as methylthio , ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio, t-butylthio, etc.; C _2-6 alkenylthio, such as vinylthio, allylthio, etc.; C _2-6 alkynylthio, such as ethynylthio , propargylthio, etc.; C _6-10 arylthio, such as phenylthio, naphthylthio, etc.; heterocyclylthio, such as thiazolylthio, pyridylthio, etc.; C _7-11 aralkylthio, such as benzylthio, phenethylthio, etc.; (C _1-6 alkylthio) carbonyl, such as (methylthio)carbonyl, (ethylthio)carbonyl, (n-propylthio)carbonyl, (isopropylthio)carbonyl, (n-butylthio)carbonyl, (isobutylthio)carbonyl, (s-butylthio)carbonyl, (t- butylthio)carbonyl, etc.; C _1-6 alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, t-butylsulfinyl, etc.; C _2-6 alkenylsulfinyl, such as allylsulfinyl, etc.; C _2-6 alkynylsulfinyl, such as propargylsulfinyl C _6-10 arylsulfinyl, such as phenylsulfinyl, etc.; heterocyclylsulfinyl, such as thiazolylsulfinyl, pyridylsulfinyl, etc.; C _7-11 aralkylsulfinyl, such as benzylsulfinyl, phenethylsulfinyl, etc.; C _1-6 alkyl Sulfonyl, such as methylsulfonyl, ethylsulfonyl, t-butylsulfonyl, etc.; C _2-6 alkenylsulfonyl, such as allylsulfonyl, etc.; C _2-6 alkynylsulfonyl, such as propargylsulfonyl, etc.; C _6-10 arylsulfonyl, such as , phenylsulfonyl, etc.; heterocyclylsulfonyl, such as thiazolylsulfonyl, pyridylsulfonyl, etc.; C _7-11 aralkylsulfonyl, such as benzylsulfonyl, phenethylsulfonyl, etc.; imidazolyl, pyrazolyl, oxazolyl, isoxazolyl 6-membered heteroaryl, such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, etc.; saturated heterocyclyl, such as aziridinyl, epoxy, pyrrolidinyl, tetrahydrofuranyl, piperidyl, piperazinyl, morpholinyl and the like; triC _1-6 alkyl-substituted silyl, such as trimethylsilyl, triethylsilyl, t-butyldimethylsilyl and the like; triphenylsilyl and the like;

Examples of halogen include, but are not particularly limited to, fluorine, chlorine, bromine, iodine, and the like.

Examples of C _1-6 alkyl are not particularly limited and include C _1-6 straight or branched chain alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert- butyl, n-pentyl, isopentyl, neopentyl, n-hexyl and the like.

Examples of C _1-4 haloalkyl are not particularly limited and are C _1-4 straight or branched alkyl substituted with 1 to 9, preferably 1 to 5 halogen atoms, such as fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2, 2,2-trichloroethyl, pentafluoroethyl, 2,2,3,3-tetrafluoropropyl, 3,3-difluoropropyl, 2,3,3-trifluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 4,4-difluorobutyl, 4,4,4-trifluorobutyl, 3,4,4-trifluorobutyl, 3,3,4 ,4-tetrafluorobutyl, 3,3,4,4-pentafluorobutyl, heptafluoroisobutyl, nonafluorobutyl and the like.

Examples of aryl include, without limitation, phenyl, 1-naphthyl, 2-naphthyl and the like.

Examples of aryl C _1-6 alkyl include, but are not limited to, fluoro(phenyl)methyl, chloro(phenyl)methyl, difluoro(phenyl)methyl, dichloro(phenyl)methyl, 1-naphthyldifluoromethyl, 2-naphthyldifluoro methyl, 1-naphthyldichloromethyl, 2-naphthyldichloromethyl and the like.

The salt of the compound represented by formula (I) may be of any kind as long as it is agriculturally acceptable. Examples of the salts include inorganic acid salts such as hydrochlorides, sulfates, nitrates and the like; organic acid salts such as acetates and methanesulfonates; alkali metal salts such as sodium salts and potassium salts; Alkaline earth metal salts such as magnesium salts, calcium salts and the like; quaternary ammonium salts such as dimethylammonium and triethylammonium salts; and the like.

The symbol n represents an integer of 0-2.

Among the compounds (I) of the present invention, preferred compounds are those in which R is C _1-6 alkyl and C _1-4 haloalkyl, and more preferred compounds (I) are those in which R is normal propyl or 2,2, The compound is 2-trifluoroethyl.

Among the compounds (I) of the present invention, preferred compounds are those in which A ¹ is C _1-6 alkyl, and other preferred compounds are those in which A ¹ is fluorine, chlorine or methyl, more preferred Compound ( ^I ) is a compound wherein A1 is methyl.

Among the compounds (I) of the present invention, preferred compounds are those in which A ² is halogen and C _1-6 alkyl, and more preferred compounds (I) are those in which A ² is fluorine, chlorine or methyl. be.

Among the compounds (I) of the present invention, preferred compounds are those in which ^B1 is hydrogen or methyl.

Among the compounds (I) of the present invention, preferred compounds are those in which B ² is C _1-4 haloalkyl or substituted or unsubstituted arylC _1-4 haloalkyl, and more preferred compounds (I) are B ² is difluoromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, heptafluoropropyl or difluoro(phenyl)methyl.

Among the compounds (I) of the present invention, preferred compounds are those in which n is an integer of 0 or 1.

The term "control" includes killing, extermination, reduction and elimination. For example, "controlling mites" includes killing mites, controlling mites, reducing mites, and eliminating mites. The same applies to the "control agent".

Methods for Preparing Isoxazole Compounds or Salts Thereof The isoxazole compounds represented by Formula (I) of the present invention can be readily prepared according to the following Reaction Schemes 1 to 3, but are limited to these methods. not.

［式中、Ｒ、Ａ^１、Ａ^２、Ｂ^１及びＢ^２は、上記定義されたとおりである。］ [Reaction Scheme 1]

[wherein R, A ¹ , A ² , B ¹ and B ² are as defined above. ]

［式中、Ｒ、Ａ^１、Ａ^２、Ｂ^１及びＢ^２は、上記定義されたとおりである。］ Step 1-1
Step 1-1 is a step of preparing compound (IV) and using hydroxylamine in the presence of a base and a solvent to produce compound (V). Depending on the type of substituents B ¹ and/or B ² , compound (V) may not be isolated in this step and undergoes a further dehydration reaction to convert to a compound of formula (Ia). (Reaction Scheme 1-1).
[Reaction Scheme 1-1]

[wherein R, A ¹ , A ² , B ¹ and B ² are as defined above. ]

The foregoing reactions are carried out in a suitable solvent or without solvent. When the above reactions are carried out in a solvent, the solvent is not limited as long as the solvent is inert to the above reactions. Examples of such solvents include fatty acids or alicyclic hydrocarbon solvents such as n-hexane, cyclohexane, n-heptane, etc.; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, etc.; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, chloroform and carbon tetrachloride; ether solvents such as diethyl ether, tetrahydrofuran (THF), 1,4-dioxane and the like; ester solvents, acetonitrile; amide solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like; and sulfoxide solvents such as dimethylsulfoxide, sulfolane, etc.; _H2O ; acetic acid, preferably methanol, ethanol and toluene. Any one of these solvents can be used alone, or two or more of them can be used in combination, if desired.

The amount of solvent used is generally 1.0 to 20 liters, preferably 1.0 to 10 liters per 1 mol of compound (IV).

The foregoing reactions can be performed with or without a base. Among the above, this reaction is preferably carried out in the presence of a base. As the base, a wide range of conventionally known bases can be used. Examples of bases include inorganic bases such as alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, sodium bicarbonate, etc.; alkali metal hydroxides such as sodium hydroxide, hydroxide potassium and the like; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylaminopyridine, piperidine, etc., preferably pyridine. Any individual one of these bases or a combination of two or more than two of them are used.

The amount of base used is generally 1.0-5.0 mol, preferably 1.0-2.0 mol, per 1 mol of compound (IV).

The hydroxylamine used is hydroxylamine hydrochloride, hydroxylamine sulfate or hydroxylamine hydrate, preferably hydroxylamine hydrochloride.

The amount of hydroxylamine used is generally 1.0-5.0 mol, preferably 1.0-2.0 mol, per 1 mol of compound (IV).

The reaction temperature varies depending on the starting compound, reaction reagent, solvent, etc., but is usually -40°C to reflux temperature, preferably 50 to 150°C, in the reaction system.

The reaction time varies depending on the present compound, reaction reagent, solvent, reaction temperature and the like, but is generally 10 minutes to 48 hours, preferably 20 minutes to 24 hours, more preferably 1 to 10 hours.

Compound (IV) used in this step is: It can be produced according to a known method (for example, the method described in JP-A-2008-260706 and WO 2007/081019).

［式中、Ｒ、Ａ^１、Ａ^２、Ｂ^１及びＢ^２は、上記定義されたとおりである。］ Step 1-2
Step 1-2 provides compound (V) and uses thionyl chloride in the presence of a base and a solvent to convert a compound of formula (I) of the present invention of formula (Ia ) (reaction scheme 1-2).
[Reaction Scheme 1-2]

[wherein R, A ¹ , A ² , B ¹ and B ² are as defined above. ]

The foregoing reactions are carried out in a suitable solvent or without solvent. When the above reactions are carried out in a solvent, the solvent is not limited as long as the solvent is inert to the above reactions. Examples of such solvents include fatty acids or alicyclic hydrocarbon solvents such as n-hexane, cyclohexane, n-heptane, etc.; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, etc.; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, chloroform and carbon tetrachloride; ether solvents such as diethyl ether, tetrahydrofuran (THF), 1,4-dioxane and the like; ester solvents, acetonitrile; amide solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like; and sulfoxide solvents such as Examples include dimethylsulfoxide and sulfolane, preferably toluene. Any one of these solvents can be used alone, or two or more of them can be used in combination, if desired.

The amount of solvent used is generally 0.5 to 20 liters, preferably 0.5 to 10 liters per 1 mol of compound (V).

The foregoing reactions can be performed with or without a base. Among the above, this reaction is preferably carried out in the presence of a base. As the base, a wide range of conventionally known bases can be used. Examples of bases include inorganic bases such as alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, sodium bicarbonate, etc.; alkali metal hydroxides such as sodium hydroxide, hydroxide potassium and the like; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylaminopyridine, piperidine, etc., preferably pyridine. Any individual one of these bases or a combination of two or more than two of them are used.

The amount of base used is generally 1.0-5.0 mol, preferably 1.0-2.0 mol, per 1 mol of compound (V).

The amount of thionyl chloride used is generally 1.0-6.0 mol, preferably 1.0-3.0 mol, per 1 mol of compound (V).

The reaction temperature varies depending on the starting compound, reaction reagent, solvent, etc., but is usually -40°C to reflux temperature, preferably 0 to 120°C, in the reaction system.

The reaction time varies depending on the present compound, reagent, solvent, reaction temperature and the like, but is generally 10 minutes to 48 hours, preferably 20 minutes to 24 hours, more preferably 1 to 10 hours.

［式中、Ｒ、Ａ^１、Ａ^２、Ｂ^１及びＢ^２は、上記定義されたとおりである。］ [Reaction Scheme 2]

[wherein R, A ¹ , A ² , B ¹ and B ² are as defined above. ]

L represents methyl or ethyl.

G represents a leaving group. Examples of leaving groups include halogens such as chlorine, bromine and iodine; substituted or unsubstituted C _1-6 alkylsulfonates; and substituted or unsubstituted arylsulfonates. Examples of substituents include the aforementioned substituents, eg halogen and C _1-6 alkyl.

［式中、Ｒ、Ａ^１、Ａ^２、Ｂ^１、Ｂ^２及びＬは、上記定義されたとおりである。］ Step 2-1
Step 2-1 is a step of preparing compound VI and using compound (VII) or compound (VIII) in the presence of a base and a solvent to produce compound (IX) (reaction scheme 2-1). .
[Reaction Scheme 2-1]

[wherein R, A ¹ , A ² , B ¹ , B ² and L are as defined above. ]

The foregoing reactions are carried out in a suitable solvent or without solvent. When the above reactions are carried out in a solvent, the solvent is not limited as long as the solvent is inert to the above reactions. Examples of such solvents include fatty acids or alicyclic hydrocarbon solvents such as n-hexane, cyclohexane, n-heptane, etc.; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, etc.; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, chloroform and carbon tetrachloride; ether solvents such as diethyl ether, tetrahydrofuran (THF), 1,4-dioxane and the like; ester solvents, acetonitrile; amide solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like; and sulfoxide solvents such as Dimethyl sulfoxide, sulfolane and the like, preferably tetrahydrofuran and N,N-dimethylformamide. Any one of these solvents can be used alone, or two or more of them can be used in combination, if desired.

The amount of solvent used is generally 0.5 to 20 liters, preferably 0.5 to 10 liters per mol of compound (VI).

The foregoing reactions can be performed with or without a base. Among the above, this reaction is preferably carried out in the presence of a base. As the base, a wide range of conventionally known bases can be used. Examples of bases include inorganic bases such as alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, sodium bicarbonate, etc.; alkali metal hydroxides such as sodium hydroxide, hydroxide potassium and the like; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; organic bases such as pyridine, triethylamine, diethylamine, and the like, preferably pyridine, sodium hydride and sodium methoxide. Any individual one of these bases or a combination of two or more than two of them are used.

The amount of base used is generally 1.0-5.0 mol, preferably 1.0-2.0 mol, per 1 mol of compound (VI).

The amount of compound (VII) or compound (VIII) used is generally 1.0-3.0 mol, preferably 1.0-2.0 mol, per 1 mol of compound (VI).

The reaction temperature varies depending on starting compounds, reagents, solvents, etc., but is usually -40°C to reflux temperature, preferably 0 to 120°C, in the reaction system.

Although the reaction time varies depending on the present compound, reagents, solvent, reaction temperature, etc., it is generally 10 minutes to 48 hours, preferably 10 minutes to 48 hours, more preferably 20 minutes to 24 hours.

［式中、Ｒ、Ａ^１、Ａ^２、Ｂ^１及びＢ^２は、上記定義されたとおりである。］ Step 2-2
Step 2-2 is a step of preparing compound (IX) and using hydroxylamine in the presence of a base and a solvent to prepare compound (X). Depending on the type of substituents B ¹ and/or B ² , compound (X) may not be isolated in this step and undergoes a further dehydration reaction to convert to a compound of formula (Ia). (Reaction Scheme 2-2).
[Reaction Scheme 2-2]

[wherein R, A ¹ , A ² , B ¹ and B ² are as defined above. ]

The foregoing reactions are carried out in a suitable solvent or without solvent. When the above reactions are carried out in a solvent, the solvent is not limited as long as the solvent is inert to the above reactions. Examples of such solvents include fatty acids or alicyclic hydrocarbon solvents such as n-hexane, cyclohexane, n-heptane, etc.; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, etc.; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, chloroform and carbon tetrachloride; ether solvents such as diethyl ether, tetrahydrofuran (THF), 1,4-dioxane and the like; ester solvents, acetonitrile; amide solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like; and sulfoxide solvents such as dimethylsulfoxide, sulfolane, etc.; _H2O ; acetic acid, preferably methanol, ethanol and toluene. Any one of these solvents can be used alone, or two or more of them can be used in combination, if desired.

The amount of solvent used is generally 1.0 to 20 liters, preferably 1.0 to 10 liters per 1 mol of compound (IX).

The foregoing reactions can be performed with or without a base. Among the above, this reaction is preferably carried out in the presence of a base. As the base, a wide range of conventionally known bases can be used. Examples of bases include inorganic bases such as alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, sodium bicarbonate, etc.; alkali metal hydroxides such as sodium hydroxide, hydroxide potassium and the like; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylaminopyridine, piperidine, etc., preferably pyridine. Any individual one of these bases or a combination of two or more than two of them are used.

The amount of base used is generally 1.0-5.0 mol, preferably 1.0-2.0 mol, per 1 mol of compound (IX).

The hydroxylamine used is hydroxylamine hydrochloride, hydroxylamine sulfate or hydroxylamine hydrate, preferably hydroxylamine hydrochloride.

The amount of hydroxylamine used is generally 1.0-5.0 mol, preferably 1.0-2.0 mol, per 1 mol of compound (IX).

The reaction temperature varies depending on the starting compound, reaction reagent, solvent, etc., but is usually -40°C to reflux temperature, preferably 50 to 150°C, in the reaction system.

Although the reaction time varies depending on the present compound, reaction reagent, solvent, reaction temperature, etc., it is generally 10 minutes to 48 hours, preferably 20 minutes to 24 hours, more preferably 1 to 10 hours.

Compound (IX) used in this step can also be produced according to known methods (eg, the method described in J. Org. Chem., 55, 1959-1964 (1990)).

［式中、Ａ^１、Ａ^２、Ｂ^１及びＢ^２は、上記定義されたとおりである。］ Step 2-3
Step 2-3 is a step of preparing compound (X) and using thionyl chloride in the presence of a base and a solvent to produce compound (XI) (reaction scheme 2-3).
[Reaction Scheme 2-3]

[wherein A ¹ , A ² , B ¹ and B ² are as defined above. ]

The foregoing reactions are carried out in a suitable solvent or without solvent. When the above reactions are carried out in a solvent, the solvent is not limited as long as the solvent is inert to the above reactions. Examples of such solvents include fatty acids or alicyclic hydrocarbon solvents such as n-hexane, cyclohexane, n-heptane, etc.; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, etc.; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, chloroform and carbon tetrachloride; ether solvents such as diethyl ether, tetrahydrofuran (THF), 1,4-dioxane and the like; ester solvents, acetonitrile; amide solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like; and sulfoxide solvents such as Examples include dimethylsulfoxide and sulfolane, preferably toluene. Any one of these solvents can be used alone, or two or more of them can be used in combination, if desired.

The amount of solvent used is generally 0.5 to 20 liters, preferably 0.5 to 10 liters per 1 mol of compound (X).

The foregoing reactions can be performed with or without a base. Among the above, this reaction is preferably carried out in the presence of a base. As the base, a wide range of conventionally known bases can be used. Examples of bases include inorganic bases such as alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, sodium bicarbonate, etc.; alkali metal hydroxides such as sodium hydroxide, hydroxide potassium and the like; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylaminopyridine, piperidine, etc., preferably pyridine. Any individual one of these bases or a combination of two or more than two of them are used.

The amount of base used is generally 1.0-5.0 mol, preferably 1.0-2.0 mol, per 1 mol of compound (X).

The amount of thionyl chloride used is generally 1.0-6.0 mol, preferably 1.0-3.0 mol, per 1 mol of compound (X).

The reaction temperature varies depending on starting compounds, reagents, solvents, etc., but is usually -40°C to reflux temperature, preferably 0 to 120°C, in the reaction system.

The reaction time varies depending on the present compound, reagent, solvent, reaction temperature and the like, but is generally 10 minutes to 48 hours, preferably 20 minutes to 24 hours, more preferably 1 to 10 hours.

［式中、Ａ^１、Ａ^２、Ｂ^１及びＢ^２は、上記定義されたとおりである。］ Step 2-4
Step 2-4 is a step of preparing compound (XI) and using chlorosulfonic acid in the absence or presence of a solvent to produce compound (XII). Compound (XII) can also be produced by sulfonation of compound (XI) followed by chlorosulfonation (reaction scheme 2-4).
[Reaction Scheme 2-4]

[wherein A ¹ , A ² , B ¹ and B ² are as defined above. ]

The reagent used for chlorosulfonation is not particularly limited, and examples thereof include chlorosulfonic acid. When using chlorosulfonic acid, this step can be done in one step. For chlorosulfonation, a two step process can be used involving sulfonation followed by chlorination. Compound (XII) can be prepared by reacting isoxazole compound (XI) with a sulfonating agent to produce HOSO ₂ -substituted compound (XI) and then reacting HOSO ₂ -containing compound (XI) with a chlorinating agent. can be manufactured.

Reagents used for sulfation are not particularly limited and, for example, chlorosulfonic acid and sulfuric acid are provided. Examples of chlorinating agents used for chlorination include, without limitation, chlorine, POCl ₃ , SOCl ₂ , SO ₂ Cl ₂ and oxalyl chloride.

When chlorosulfonic acid is used, the proportion of compound (XI) and chlorosulfonic acid used in the reaction is not particularly limited and can be appropriately selected from a wide range. The amount of chlorosulfonic acid used is generally 1.0-50 mol, preferably 2.0-20 mol, per 1 mol of compound (XI).

When a sulfonating reagent and a chlorinating agent are used, the ratio of the sulfonating reagent to the chlorinating agent in the reaction between compound (XI) and the sulfonating agent is not particularly limited, and can be appropriately selected from a wide range. can do. The amount of sulfonating reagent used is generally 1.0 to 50 mol, preferably 1.0 to 20 mol, per 1 mol of compound (XI). The ratio of use in the reaction between compound (XI) and the chlorinating agent is not particularly limited and can be appropriately selected from a wide range. The amount of chlorinating agent used is generally 1.0-50 mol, preferably 1.0-20 mol, per 1 mol of compound (XI).

The foregoing reactions are carried out in a suitable solvent or without solvent. When the above reactions are carried out in a solvent, the solvent is not limited as long as the solvent is inert to the above reactions. Examples of such solvents include halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, chloroform and carbon tetrachloride, preferably chloroform.

The amount of solvent used is generally 1.0 to 20 liters, preferably 1.0 to 10 liters per 1 mol of compound (XI).

The reaction temperature varies depending on starting compounds, reagents, solvents, etc., but is usually -40°C to reflux temperature, preferably 0 to 80°C, in the reaction system.

The reaction time varies depending on the present compound, reagents, solvent, reaction temperature and the like, but is generally 10 minutes to 48 hours, preferably 5 minutes to 24 hours.

［式中、Ａ^１、Ａ^２、Ｂ^１及びＢ^２は、上記定義されたとおりである。］ Step 2-5
Step 2-5 is a step of preparing a reducing agent and compound (XII) in the presence or absence of a solvent to produce compound (XIII) (reaction scheme 2-5).
[Reaction Scheme 2-5]

[wherein A ¹ , A ² , B ¹ and B ² are as defined above. ]

The ratio of compound (XII) and reducing agent used in this reaction is not particularly limited and can be appropriately selected from a wide range.

Any of conventionally known reducing agents can be widely used as the reducing agent. Examples of reducing agents include phosphorus compounds such as triphenylphosphine; reducing agents containing metals and acids such as zinc and acid, tin(II) and acid and iron and acid; and specific reducing agents such as Reducing agents such as red phosphorus, iodine, dichlorodimethylsilane-zinc-dimethylacetamide, and lithium aluminum hydride can be used. Examples of acids include organic acids such as acetic acid; and inorganic acids such as hydrochloric acid, sulfuric acid and the like.

The ratio of compound (XII) and reducing agent used in this reaction is not particularly limited and can be appropriately selected from a wide range.

The amounts of zinc and acid used are generally 1.0-50.0 mol, preferably 1.0-20.0 mol, per 1 mol of compound (XII).

The foregoing reactions are carried out in a suitable solvent. There is no limitation on the solvent as long as the solvent is inert to the reaction. Examples of such solvents include H ₂ O; carboxylic acid solvents such as acetic acid, propionic acid and the like; alcoholic solvents such as methanol, ethanol, n-propanol, isopropanol and the like. Any one of these solvents can be used alone, or two or more of them can be used in combination, if desired. Preferably _H2O and an alcohol, more preferably _H2O and isopropanol can be used.

The amount of solvent used is generally 1.0 to 20 liters, preferably 1.0 to 10 liters per mol of compound (XII).

The reaction temperature varies depending on the starting compound, reaction reagent, solvent, etc., but is usually -40°C to reflux temperature, preferably 0 to 150°C, in the reaction system.

The reaction time varies depending on the present compound, reagents, solvent, reaction temperature and the like, but is generally 10 minutes to 48 hours, preferably 5 minutes to 24 hours.

［式中、Ｒ、Ａ^１、Ａ^２、Ｂ^１、Ｂ^２及びＧは、上記定義されたとおりである。］ Step 2-6
Step 2-6 provides compound (XIII) using an alkylating agent (XIV) in the presence of a base and a solvent, wherein n is 0 in compounds of formula (I) of the present invention This is a step for producing a compound represented by formula (Ia) (reaction scheme 2-6).
[Reaction Scheme 2-6]

[wherein R, A ¹ , A ² , B ¹ , B ² and G are as defined above. ]

The ratio of the thiol compound (XIII) and the alkyl reagent (XIV) used in this reaction is not particularly limited and can be appropriately selected from a wide range. The amount of alkyl reagent (XIV) used is generally 1.0-5.0 mol, preferably 1.0-2.0 mol, per 1 mol of compound (XIII).

The foregoing reactions can be performed with or without a base. Among the above, this reaction is preferably carried out in the presence of a base. As the base, a wide range of conventionally known bases can be used. Examples of bases include inorganic bases such as alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, sodium bicarbonate, etc.; alkali metal hydroxides such as sodium hydroxide, hydroxide potassium and the like; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like; organic bases such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylaminopyridine, piperidine and the like; preferably alkali metal carbonates and alkali metal hydrides, more preferably sodium carbonate and potassium carbonate , potassium bicarbonate, sodium bicarbonate and sodium hydride. Any individual one of these bases or a combination of two or more than two of them are used.

The amount of base used is generally 1.0-5.0 mol, preferably 1.0-3.0 mol, per 1 mol of compound (XIII).

The aforementioned reaction can be carried out additionally by adding a radical initiator. Examples of radical initiators include, but are not limited to, sulfurous acid, sulfites, longalite (compound name: sodium formaldehyde sulfoxylate), sulfite adducts, and the like. Bases and radical initiators can be used in combination.

When a radical initiator is used, the amount of the radical initiator to be added is generally 0.1 to 10.0 mol, preferably 0.1 to 5.0 mol, per 1 mol of compound (XIII). be.

The foregoing reactions are carried out in a suitable solvent. Examples of solvents include fatty acids or alicyclic hydrocarbon solvents such as n-hexane, cyclohexane, n-heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene; Hydrogen solvents such as methylene chloride, 1,2-dichloroethane, chloroform and carbon tetrachloride; ether solvents such as diethyl ether, THF, 1,4-dioxane; ester solvents such as methyl acetate and acetic acid. Ethyl and the like; acetonitrile; amide solvents such as DMF, N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like; sulfoxide solvents such as dimethylsulfoxide and sulfolane; polar solvents such as alcohol solvents, For example, methanol, ethanol, isopropyl alcohol and the like; water; and the like. Any one of these solvents can be used alone, or two or more of them can be used in combination, if desired.

The amount of solvent used is generally 1.0 to 20 liters, preferably 1.0 to 10 liters per 1 mol of compound (XIII).

The reaction temperature varies depending on starting compounds, reagents, solvents, etc., but is usually -40°C to reflux temperature, preferably 0 to 100°C, in the reaction system.

The reaction time varies depending on the present compound, reagents, solvent, reaction temperature and the like, but is generally 5 minutes to 48 hours, preferably 10 minutes to 24 hours.

The compound of formula (Ia) obtained by the method shown in steps 2-6 is readily isolated from the reaction mixture and subjected to typical isolation and purification procedures such as filtration, solvent extraction, distillation. , recrystallization, column chromatography, and the like. After completion of the reaction, the compound represented by formula (Ia) can be provided to the next reaction without being isolated from the reaction system.

［式中、ｎ’は、１～２の整数を表す。Ｒ、Ａ^１、Ａ^２、Ｂ^１及びＢ^２は、上記定義されたとおりである。］ [Reaction Scheme 3]
Step 3
Step 3 provides a compound of formula (Ia), using an oxidizing agent in the presence of a solvent, in compounds of formula (I) of the present invention wherein n is 1 and 2 This is a step of preparing a compound represented by formula (Ib) (reaction scheme 3).
[Reaction Scheme 3]

[In the formula, n′ represents an integer of 1 to 2. R, A ¹ , A ² , B ¹ and B ² are as defined above. ]

The foregoing reactions are carried out in a suitable solvent or without solvent. When the above reactions are carried out in a solvent, the solvent is not limited as long as the solvent is inert to the above reactions. Examples of such solvents include fatty acids or alicyclic hydrocarbon solvents such as n-hexane, cyclohexane, n-heptane, etc.; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, etc.; halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, chloroform and carbon tetrachloride; ether solvents such as diethyl ether, tetrahydrofuran (THF), 1,4-dioxane and the like; ester solvents, For example, methyl acetate, ethyl acetate, etc.; acetonitrile; amide solvents, such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methyl-2-pyrrolidone, etc.; and ketone solvents, such as, acetone, methyl ethyl ketone, cyclohexanone, etc.; and sulfoxide solvents such as dimethylsulfoxide, sulfolane, etc.; H ₂ O; acetic acid, preferably methylene chloride, chloroform, methanol, ethanol and toluene. Any one of these solvents can be used alone, or two or more of them can be used in combination, if desired.

The amount of solvent used is usually 0.5 to 20 liters, preferably 0.5 to 10 liters per mol of compound of formula (Ia).

The aforementioned reactions can be carried out in the presence of an oxidizing agent. As the oxidizing agent, any known oxidizing agent can be used as long as the oxidizing agent is capable of oxidizing sulfide to sulfoxide. Examples of oxidizing agents include peracids such as performic acid, peracetic acid, pertrifluoroacetic acid, perbenzoic acid, m-chloroperbenzoic acid (mCPBA), o-carbonyl perbenzoic acid, etc.; alkyl hydroperoxides such as , hydrogen peroxide, t-butyl hydroperoxide, cumene hydroperoxide, etc.; and titanium tetraalkoxides, such as titanium tetraisopropoxide, etc.; Potassium, etc.; permanganates, such as permanganic acid, sodium permanganate, potassium permanganate; be done. Any separate one of these oxidizing agents or a combination of two or more than two of them are used.

The amount of base used is generally 1.0 to 10.0 mol, preferably 1.0 to 5.0 mol, per mol of the compound of formula (Ia).

The aforementioned reactions can be further carried out by adding a catalyst.

The reaction temperature varies depending on starting compounds, reagents, solvents, etc., but is usually -20°C to reflux temperature, preferably -10 to 60°C, in the reaction system.

The reaction time varies depending on the present compound, reagents, solvent, reaction temperature and the like, but is generally 10 minutes to 48 hours, preferably 20 minutes to 24 hours.

The compound of formula (Ib) obtained by the method shown in step 3 is readily isolated from the reaction mixture and subjected to typical isolation and purification procedures such as filtration, solvent extraction, distillation, repurification. Purified by the use of crystallization, chromatography, and the like.

Each compound of formula (I) obtained after completion of the reactions shown in Reaction Schemes 1 to 3 can be easily isolated from the reaction mixture using known isolation and purification techniques, such as It can be purified by filtration, solvent extraction, distillation, recrystallization and column chromatography.

The mite and nematode control agent of the present invention may, if necessary, contain additive components (carriers) commonly used in agricultural chemical formulations.

Additive components include carriers (e.g., solid carriers or liquid carriers), surfactants, binders or tackifiers, thickeners, colorants, spreading agents, adhesives, antifreeze agents, anti-caking agents, disintegrants. , antidegradants, and the like. If desired, other additive ingredients such as disinfectants, plant chips, etc. can be used. These additive components may be used singly or in combination of two or more than two.

The additive component will be described.

Solid supports include, for example, mineral supports such as pyrophyllite clay, kaolin clay, silica stone clay, talc, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, attapalgus clay, vermiculite, perlite, pumice, white carbon. (e.g. synthetic silicic acid or synthetic silicate), titanium dioxide, etc.; dextrins, sugars, etc.; inorganic salt carriers, such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride, etc.; and polymeric carriers, such as polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, urea-aldehyde. It can be a resin or the like.

Liquid carriers include, for example, monohydric alcohols such as methanol, ethanol, propanol, isopropanol, butanol, cyclohexanol, etc.; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, glycerin, etc.; polyhydric alcohol derivatives, such as propylene glycol ether; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, isophorone, etc.; ethers, such as ethyl ether, 1,4-dioxane, cellosolve , dipropyl ether, tetrahydrofuran, etc.; aliphatic hydrocarbons, such as normal paraffin, naphthene, isoparaffin, kerosene, mineral oil, etc.; aromatic hydrocarbons, such as toluene, C _9-10 alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, High-boiling aromatic hydrocarbons, etc.; Halogenated hydrocarbons, such as 1,2-dichloroethane, chloroform, carbon tetrachloride, etc.; Esters, such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate lactones, such as γ-butyrolactone; amides, such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone; nitriles, such as acetonitrile; sulfur compounds, such as dimethylsulfoxide; vegetable oils, such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, castor oil, etc.; and water.

Surfactants are not particularly limited. However, the surfactant preferably gels or swells in water. Surfactants include, for example, nonionic surfactants such as sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether-formalin condensate, polyoxyethylene polyoxypropylene block polymer, alkylpolyoxyethylene polypropylene block polymer ether, poly Oxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylenebenzyl phenyl ether, polyoxyalkylene styrylphenyl ether, acetylene diol, polyoxyalkylene-added acetylene diol, polyoxyethylene ether type silicone, ester type silicones, fluorine-containing surfactants, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, etc.; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates salt, polyoxyethylene styrylphenyl ether sulfate, alkylbenzenesulfonate, ligninsulfonate, alkylsulfosuccinate, naphthalenesulfonate, alkylnaphthalenesulfonate, naphthalenesulfonic acid-formalin condensate salt, alkylnaphthalenesulfonic acid - formalin condensate salts, fatty acid salts, polycarboxylates, N-methyl-fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkylphenyl ether phosphates, etc.; alkylamine salts, such as , laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride, etc.; and zwitterionic surfactants, such as , betaine type (e.g. dialkyldiaminoethylbetaine or alkyldimethylbenzylbetaine), amino acid type (e.g. dialkylaminoethylglycine or alkyldimethylbetaine). ngylglycine) and the like.

Binders and tackifiers include, for example, carboxymethylcellulose or its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, average molecular weight 6,000. polyethylene glycol with ˜20,000, polyethylene oxide with average molecular weight of 100,000 to 5,000,000 and natural phospholipids such as cephalic acid or lecithin.

Thickeners include, for example, water-soluble polymers such as xanthan gum, guar gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch derivatives, polysaccharides; and inorganic fine powders such as high-purity bentonite, white carbon. etc.

Colorants can be, for example, inorganic pigments such as iron oxide, titanium oxide, Prussian blue, etc. and organic dyes such as alizarin dyes, azo dyes, metal phthalocyanine dyes, and the like.

Examples of spreading agents include silicone surfactants, cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, maleic acid and styrene, methacrylic acid copolymers, polyhydric alcohol polymers and dicarboxylic acid anhydrides. and a water-soluble salt of polystyrene sulfonic acid.

Adhesives include, for example, surfactants (e.g., sodium dialkylsulfosuccinate, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers or polyoxyethylene fatty acid esters), paraffins, terpenes, polyamide resins, polyacrylates, poly Oxyethylene, waxes, polyvinyl alkyl ethers, alkylphenol-formalin condensates and synthetic resin emulsions.

Antifreeze agents can be, for example, polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol or glycerin.

Anti-caking agents can be, for example, polysaccharides (eg starch, alginic acid, mannose or galactose), polyvinylpyrrolidone, white carbon, ester gums and petroleum resins.

Disintegrants include, for example, sodium tripolyphosphate, sodium hexametaphosphate, metal stearates, cellulose powder, dextrin, methacrylic acid ester copolymers, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers and starch. It can be a polyacrylonitrile graft copolymer.

Antidegradants include, for example, desiccants such as zeolite, quicklime, magnesium oxide; antioxidants such as phenols, amines, sulfur, phosphoric acid; ultraviolet absorbers such as salicylic acid and benzophenone. system, and so on.

When the present pest control agent contains the additive components mentioned above, their content on a mass basis is usually 5 to 95%, preferably 20%, in the case of a carrier (for example, a solid carrier or a liquid carrier). ~90%, usually 0.1-30%, preferably 0.5-10% for surfactants, usually 0.1-30%, preferably 0.1-30% for other additives It is selected in the range of 0.5-10%.

This pest control agent includes powders, powder-granule mixtures, granules, wettable powders, water-soluble concentrates, water-dispersible granules, tablets, Jumbo, emulsifiable concentrates, oil formulations, solutions, flowable concentrates, emulsions. , microemulsions, suspoemulsions, ultra-low volume formulations, microcapsules, fumigants, aerosols, baits, pastes and the like.

In the actual use of the formulation, the formulation can be used as such or after being diluted with a diluent (eg water) to a given concentration. Application of formulations containing the compound or its diluted product can be done by commonly used methods such as dispersion (e.g. spraying, atomization, atomization, powder dispersion, granule dispersion, water surface dispersion or inbox dispersion). , soil application (eg, mixing or dipping), surface application (eg, coating, powder coating or covering), dipping, bait, smoking, and the like. In order to prevent the infestation and growth of harmful pests, especially harmful insects in livestock manure, it is also possible to mix the active ingredients mentioned above with livestock feed.

The ratio (% by mass) of the active ingredient in the pest control agent is appropriately selected according to need. The active ingredient is appropriately selected, for example, within the following range.
In powder formulations, powder mixtures, etc.,
0.01-20%, preferably 0.05-10%
In granules, etc.,
0.1-30%, preferably 0.5-20%
Wettable powders, water-dispersible granules, etc.
1-70%, preferably 5-50%
In water-soluble concentrates, solutions, etc.,
1-95%, preferably 10-80%
In emulsifiable concentrates, etc.,
5-90%, preferably 10-80%
In oil formulations, etc.,
1-50%, preferably 5-30%
In fluid concentrates, etc.,
5-60%, preferably 10-50%
In emulsions, microemulsions, suspoemulsions, etc.,
5-70%, preferably 10-60%
In tablets, baits, pastes, etc.,
1-80%, preferably 5-50%
In smoking agents, etc.,
0.1-50%, preferably 1-30%
In aerosols, etc.,
0.05-20%, preferably 0.1-10%

The formulations are sprayed on or applied directly after being diluted to the appropriate concentration.

When the pest control agent is used after being diluted with a diluent, the concentration of active ingredient is generally from 0.1 to 5,000 ppm. When the preparation itself is used, the applied amount per unit area is 0.1 to 5,000 g per ha in terms of the active ingredient compound, but the applied amount is not limited to this.

The present pest control agent is sufficiently effective when the present compound is used alone as an active ingredient. However, the pest control agent may optionally contain fertilizers and pesticides such as insecticides, acaricides, nematicides, synergists, fungicides, antiviral agents, attractants, herbicides, plant growth agents. It may be mixed with a control agent or the like, or used in combination therewith. In this case, a higher effect is exhibited.

The following are examples of known insecticide, acaricide, nematicide and synergist compounds, which may be mixed or used in combination.

1. Acetylcholinesterase inhibitors (1A) carbamate series: alanycarb, aldicarb, aldoxycarb, bendiocarb, benfuracarb, butocarbboxim, butoxycarboxim ( butoxycarbboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimetacarb, XMC (bamidthion (vamidothion), xylylcarb;

(1B) Organophosphorus: acephate, azamethiphos, azinphosethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos , chlormephos, chlorpyrifos, chlorpyrifosmethyl, coumaphos, cyanophos, demeton-S-methyl, diamidaphos, diazinon, Dichlorvos, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, DSP (O,O-diethyl O-(4-dimethylsulfur moylphenyl)phosphorothioate), EPN (O-ethyl O-4-nitrophenyl phenylphosphonothioate), ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion fenitrothion, fenthion, fonofos, fosthiazate, fosthietan, heptenophos, isamidofos, isazophos, isofenphos-methyl, isopropyl O - (methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled ed), omethoate, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, phenthoate, forate, fosalone ( phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propaphos, propetamphos, prothiofos, pyraclophos (pyraclofos), pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, thionazin ), triazophos, trichlorfon, vamidothion, dichlofenthion, imicyafos, isocarbophos, mesulfenfos, flupyrazofos

2. GABAergic chloride channel antagonists (2A) cyclic diene organochlorines: chlordane, endosulfan, gamma-BHC (benzene hexachloride);

(2B) Phenylpyrazole series: acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, RZI-02-003 (code number)

3. Sodium channel modulators (3A) pyrethroids/pyrethrins: acrinathrin, allethrin (including d-cis-trans and d-trans), bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl S-cyclopentenyl), bioresmethrin, cycloprothrin, cyfluthrin (including beta-), cyhalothrin (including gamma- and lambda-), cypermethrin (alpha- , beta-, theta- and zeta-), cyphenothrin [including (IR)-trans-isomer], deltamethrin, empenthrin, esfenvalerate, etofen etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, halfenprox, imiprothrin, metofluthrin, permethrin ), phenothrin [including (IR)-trans-isomers], prallethrin, profluthrin, pyrethrin, resmethrin, RU15525 (code number), silafluofen, Tefluthrin, tetramethrin, tralomethrin, transfluthrin, ZX18901 (code number), fluvalinate (including tau-), tetramethylfluthrin, meperfluthrin;

(3B) DDT/Methoxychlor: DDT (1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane), methoxychlor

3. Nicotinic Acetylcholine Receptor Agonists/Antagonists (4A) Neonicotinoids: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam );

(4B) nicotine: nicotine sulfate

4. nicotinic acetylcholine receptor allosteric activator agents Spinosine: spinetoram, spinosad

5. Chloride channel activators Abamectins, Milbemycins: abamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, polynactin )

6. juvenile hormone analogues diofenolan, hydroprene, kinoprene, methothrin, fenoxycarb, pyriproxyfen

7. Other non-specific (multi-site) inhibitors 1,3-dichloropropene, DCIP (bis(2-chloro-1-methylethyl) ether), ethylene dibromide, methyl bromide, chloropicrin, sulfuryl fluoride

8. antifeedant pymetrozine, flonicamid, pyrifluquinazon

9. Mite growth inhibitors clofentezine, diflovidazin, hexythiazox, etoxazole

10. Microorganism-derived insect midgut lining agent BT (Bacillus thuringiensis) agent: Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. israelensis), Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt crop proteins (CrylAb, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1), Bacillus popilliae, Bacillus subtilis

11. Mitochondrial ATP synthase inhibitor diafenthiuron; organotin acaricides: azocyclotin, cyhexatin, fenbutatin oxide; propargite, tetradifon

12. Oxidative phosphorylation uncoupler chlorfenapyr, DNOC (6-methyl-2,4-dinitrophenol) by perturbation of the proton gradient

13. Nicotinic Acetylcholine Receptor Channel Blocker Nereis Toxin Analogs: bensultap, cartap, thiocyclam, thiosultap

14. chitin biosynthesis inhibitor, type 0
benzoyl urea: bistrifluron, chlorfluazoron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, fluazuron

15. chitin biosynthesis inhibitor, type 1
buprofezin

16. Molting inhibitor, Diptera cyromazine

17. Ecdysone receptor agonist (promoting molting)
Diacylhydrazines: chromafenozide, halofenozide, methoxyfenozide, tebufenozide

18. Octopamine receptor agonist amitraz

19. Mitochondrial electron transport chain complex III inhibitors hydramethylnon, acequinocyl, fluacrypyrim, cyenopyrafen

20. Mitochondrial electron transport chain complex II inhibitors cyflumetofen, cyenopyrafen, NNI-0711 (code number)

21. Mitochondrial Electron Transport Chain Complex I Inhibitor (METI)
METI acaricides and insecticides: fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad

Other: rotenone

22. sodium channel blockers indoxacarb, metaflumizon

23. Lipid synthesis inhibitors Tetronic acid and tetramic acid derivatives: spirodiclofen, spiromesifen, spirotetramat

24. Mitochondrial electron transport chain complex IV inhibitor Aluminum phosphide, phosphine, zinc phosphide, calcium cyanide

25. Neuroinhibitor (mechanism of action unknown)
bifenazate

26. aconitase inhibitor sodium fluoroacetate

27. Synergist piperonyl butoxide, DEF (phosphorotrithioic acid S,S,S-tributyl ester)

28. ryanodine receptor modulators chlorantraniliprole, flubendiamide, cyantraniliprole

29. Compounds with unknown mechanism of action azadirachtin, amidoflumet, benclothiaz, benzoximate, bromopropylate, chinomethionat, CL900167 (code number), cryolite, dicofol, dicyclanil, dienochlor, dinobuton, fenbutatin oxide, fenothiocarb, fluensulfone, flufenerim, flsulfamide, carandin ( karanjin, metham, methoprene, methoxyfenozide, methyl isothiocyanate, pyridalyl, pyrifluquinazon, sulcofuron-sodium, sulfluramid, sulfoxaflor , flupyradifurone, flometoquin, IKI-3106 (code number)

30. entomopathogenic filamentous fungi, nematopathogenic microorganisms Beauveria bassiana, Beauveria tenella, Verticillium lecanii, Pacilimyces tenuipes, Pecilomyces humosoroseus ( Paecilomyces fumosoroceus), Beauveria brongniartii, Monacrosporium phymatophagum, Pasteuriapenetrans

32. sex pheromone (Z)-11-hexadecenal, (Z)-11-hexadecenyl acetate, litlure-A, litlure-B, Z-13-eicosen-10-one, (Z,E)-9,12-tetradecadienyl acetate, (Z)-9-tetradecen-1-ol, (Z)-11-tetradecenyl acetate, (Z)-9,12-tetradeca dienyl acetate, (Z,E)-9,11-tetradecadienyl acetate

The following are examples of known fungicide or disease damage control compounds that can be mixed or used in combination.

1. Nucleic Acid Biosynthesis Inhibitors Acylalanines: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M;
Oxazolidinones: oxadixyl;
Butyrolactones: clozylacone, ofurace;
Hydroxy-(2-amino)pyrimidines: bupirimate, dimethirimol, ethirimol;
isoxazole: hymexazol;
isothiazolones: octhilinone;
Carboxylic acid: oxolinic acid

2. mitotic and cytostatic benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
Thiophanates: thiophanate, thiophanate-methyl;
N-Phenylcarbamates: diethofencarb;
Toluamides: zoxamide;
Phenylureas: pencycuron;
pyridinylmethylbenzamides: fluopicolide

3. Respiratory Inhibitor Pyrimidine Amines: Diflumetorim;
Carboxamides: benodanil, flutolanil, mepronil, fluopyram, fenfuram, carboxin, oxycarboxin, thifluzamide, bixafen , furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, fluxapyroxad, isofetamide, benzovindiflupyr );
Methoxy-acrylates: azoxystrobin, enestroburin, picoxystrobin, pyraoxystrobin, coumoxystrobin, enoxastrobin , flufenoxystrobin;
Methoxy-carbamates: pyraclostrobin, pyrametostrobin, triclopyricarb;
oximinoacetic acids: kresoxim-methyl, trifloxystrobin;
oximinoacetamides: dimoxystrobin, metominostrobin, orysastrobin, fenaminstrobin;
Oxazolidinediones: famoxadone;
Dihydrodioxazines: fluoxastrobin;
Imidazolinones: fenamidone;
Benzyl-carbamates: pyribencarb;
Cyanoimidazoles: cyazofamid;
Sulfamoyl triazoles: amisulbrom;
Dinitrophenylcrotonic acids: binapacryl, methyldinocap, dinocap;
2,6-dinitro-anilines: fluazinam;
pyrimidinone hydrazones: ferimzone;
triphenyltin: TPTA, TPTC, TPTH;
Thiophenecarboxamides: silthiofam
Triazolopyrimidylamine: ametoctradin

4. amino acid and protein synthesis inhibitors anilinopyrimidines: cyprodinil, mepanipyrim, pyrimethanil;
enopyranuronic acids: blasticidin-S, mildiomycin;
Hexopyranosyl antibiotics: kasugamycin;
Glucopyranosyl antibiotics: streptomycin;
Tetracycline antibiotics: oxytetracycline

5. signal transduction pathway inhibitor quinoline: quinoxyfen;
Quinazolines: proquinazid;
Phenylpyrroles: fenpiclonil, fludioxonil;
Dicarboximides: chlozolinate, iprodione, procymidone, vinclozolin

6. lipid synthesis and membrane integrity inhibitors phosphorothiolates: edifenphos, iprobenfos, pyrazophos;
Dithiolanes: isoprothiolane;
Aromatic hydrocarbons: biphenyl, chloroneb, dichloran, quintozene, tecnazene, tolclofos-methyl;
1,2,4-thiadiazole: etridiazole;
Carbamates: iodocarb, propamocarb-hydrochloride, prothiocarb;
cinnamic acid amides: dimethomorph, flumorph;
Valinamidocarbamates: benthiavalicarb-isopropyl, iprovalicarb, valifenalate;
mandelic acid amide: mandipropamid;
Bacillus subtilis and the bactericidal lipopeptides produced: Bacillus subtilis (strain: QST713)

7. Inhibitors piperazines of sterol biosynthesis in membranes: triforine;
pyridines: pyrifenox;
pyrimidines: fenarimol, nuarimol;
Imidazoles: imazalil, oxpoconazole-fumarate, pefurazoate, prochloraz, triflumizole;
Triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole ( epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole ( ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon (triadimefon), triadimenol, triticonazole, furconazole, fluconazole-cis, quinconazole;
Morpholines: aldimorph, dodemorph, fenpropimorph, tridemorph;
piperidines: fenpropidin, piperalin;
Spiroketal amines: spiroxamine;
hydroxyanilides: fenhexamid;
Thiocarbamates: pyributicarb;
Allylamines: naftifine, terbinafine

8. glucan synthesis inhibitors glucopyranosyl-type antibiotics: validamycin;
Peptidylpyridine nucleotide compounds: polyoxins

9. melanin synthesis inhibitor isobenzofuranone: phthalide;
pyrroloquinoline: pyroquilon;
triazolobenzothiazole: tricyclazole;
carboxamides: carpropamid, diclocymet;
Propionamide: fenoxanil

10. Host plant resistance inducers benzothiadiazoles: acibenzolar-S-methyl;
Benzisothiazoles: probenazole;
Thiadiazolecarboxamides: tiadinil, isotianil
Natural product: laminarin

11. Compounds with unknown mechanism of action Copper compounds: copper hydroxide, copper dioctoate, basic copper chloride, copper sulfate, cuprous oxide, oxine-copper, Bordeaux mixture, copper nonylphenol sulfonate;
sulfur compounds: sulfur;
Dithiocarbamates: ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram, cufraneb;
phthalimides: captan, folpet, captafol;
Chloronitriles: chlorothalonil;
Sulfamides: dichlofluanid, tolylfluanid;
Guanidines: guazatine, iminoctadine-albesilate, iminoctadine-triacetate, dodine;

Other compounds: anilazine, dithianon, cymoxanil, fosetyl (aluminum, calcium, sodium), phosphoric acid and salts, tecloftalam, triazoxide, flusulfamide , diclomezine, methasulfocarb, ethaboxam, cyflufenamid, metrafenone, potassium bicarbonate, sodium bicarbonate, BAF-045 (code number), (5,7-dimethoxy -2-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine), BAG-010 (code number), benthiazole, bronopol , carvone, chinomethionate, dazomet, DBEDC, debacarb, dichlorophen, difenzoquat-methyl sulfate, dimethyl disulfide, diphenylamine, ethoxyquin ( ethoxyquin), flumetover, fluoroimide, flutianil, furocarboxylic acid, metam, nabam, natamycin, nitrapyrin, nitrothal-isopropyl, o - phenylphenol, oxazinylazole, oxyquinoline sulfate, phenazine oxide, polycarbamates, pyriofenone, fenpyrazamine, silver, pyrisoxazole, Tebufloquin, tolnifanide, trichlamide, mineral oil, organic oil, tolproca tolprocarb, oxathiapiprolin

Below are examples of known herbicide compounds and plant growth regulators that can be mixed or used in combination.
A1. Acetyl-CoA carboxylase (ACCase) inhibitors (A1-1) aryloxyphenoxypropionates: clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, diclofop-P-methyl, fenoxaprop-P-ethyl, fluazifop-butyl, fluazifop-P-butyl , haloxyfop, haloxyfop-etotyl, haloxyfop-P, metamifop, propaquizafop, quizalofop-ethyl, quizalofop- P-ethyl, quizalofop-P-tefuryl, fenthiaprop-ethyl;

(A1-2) Cyclohexanediones: alloxydim, butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim ;

(A1-3) phenylpyrazolines: aminopyralid, pinoxaden;

B. Acetolactate synthase (ALS) inhibitor (B-1) imidazolinones: imazamethabenz-methyl, imazamox, imazapic (including salts with amines, etc.), imazapyr (including salts with isopropylamine, etc.), imazaquin, imazathapyr;

(B-2) pyrimidinyloxybenzoate: bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, pyrithiobac-sodium pyrimisulfan, triafamone;

(B-3) Sulfonylaminocarbonyltriazolinones: flucarbazone-sodium, thiencarbazone (including sodium salts, methyl esters, etc.), propoxycarbazone-sodium, procarbazone sodium ( procarbazone-sodium), iofensulfuron-sodium;

(B-4) sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron ), cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron-methyl-sodium, foramus foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl-sodium, mesosulfuron-methyl, thifensulfuron-methyl methyl), triasulfuron, tribenuron-methyl, trifloxysulfuron-sodium, triflusulfuron-methyl, tritosulfuron, orthosulfuron orthosulfamuron, propgirisulfuron, metazosulfuron, flucetosulfuron;

(B-5) triazolopyrimidines: cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, pyroxsulam;

C1. Inhibitors of photosynthesis in photosystem II (1)
(C1-1) phenyl carbamates: desmedipham, phenmedipham;
(C1-2) Pyridazinones: chloridazon, brompyrazon;
(C1-3) triazines: ametryn, atrazine, cyanazine, desmetryne, dimethametryn, eglinazine-ethyl, prometon, prometryn ( prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryn, trietazine;
(C1-4) triazinones: metamitron, metribuzin;
(C1-5) triazolinones: amicarbazone;
(C1-6) uracils: bromacil, lenacil, terbacil;

C2. Inhibitors of photosynthesis in photosystem II (2)
(C2-1) amides: pentanochlor, propanil;
(C2-2) ureas: chlorbromuron, chlorotoluron, chloroxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron (tebuthiuron), metobenzuron;

C3. Inhibitors of photosynthesis in photosystem II (3)
(C3-1) benzothiadiazones: bentazone;
(C3-2) nitriles: bromofenoxim, bromoxynil (including esters such as butyric acid, octanoic acid, heptanoic acid), ioxynil;
(C3-3) phenylpyrazines: pyridafol, pyridate;

D. Photosystem I electron acceptor (D-1) bipyridylium: diquat, paraquat dichloride;

E. Protoporphyrinogen oxidase (PPO) inhibitors (E-1) diphenyl ethers: acifluorfen-sodium, bifenox, chlomethoxyfen, ethoxyfen-ethyl, fluoro fluoroglycofen-ethyl, fomesafen, lactofen, oxyfluorfen;
(E-2) N-phenylphthalimides: cinidon-ethyl, flumiclorac-pentyl, flumioxazin, chlorphthalim;
(E-3) oxydiazoles: oxadiargyl, oxadiazon;
(E-4) oxazolidinediones: pentoxazone;
(E-5) phenylpyrazoles: fluazolate, pyraflufen-ethyl;
(E-6) pyrimidinediones: benzfendizone, butafenacil, saflufenacil, tiafenacil;
(E-7) thiadiazoles: fluthiacet-methyl, thidiazimin;
(E-8) triazolinones: azafenidin, carfentrazone-ethyl, sulfentrazone, bencarbazone;
(E-9) Other compounds: flufenpyr-ethyl, profluazol, pyraclonil, SYP-298 (code number), SYP-300 (code number);

F1. Inhibitors of carotenoid biosynthesis at the phytoene desaturase stage (PDS) (F1-1) pyridazinones: norflurazon;
(F1-2) pyrimidinecarboxamides: diflufenican, picolinafen;
(F1-3) Other compounds: beflubutamid, fluridone, flurochloridone, flurtamone;

F2. 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (F2-1) Callistemones: mesotrione;
(F2-2) isoxazoles: pyrasulfotole, isoxaflutole, isoxachlortole;
(F2-3) pyrazoles: benzofenap, pyrazolinate, pyrazoxyfen, topramezone;
(F2-4) triketones: sulcotrione, tefuryltrione, tembotrione, pyrasulfotole, topramezone, bicyclopyrone;

F3. Carotenoid biosynthesis inhibitor (target unknown)
(F3-1) diphenyl ethers: acronifen;
(F3-2) isoxazolidinones: clomazone;
(F3-3) triazoles: amitrole;

G. EPSP synthase inhibitor (aromatic amino acid biosynthesis inhibitor)
(G-1) Glycines: glyphosate (including salts such as sodium, amine, propylamine, isopropylamine, dimethylamine, trimesium);

H. Glutamine synthetase inhibitor (H-1) phosphinic acids: bilanafos, glufosinate (including salts of amines, sodium, etc.);

I. Dihydropteroic Acid (DHP) Synthase Inhibitors (I-1) Carbamates: Asuram;

K1. microtubule polymerization inhibitor (K1-1) benzamides: propyzamide, tebutam;
(K1-2) benzoic acids: chlorthal-dimethyl;
(K1-3) Dinitroanilines: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine ), trifluralin;
(K1-4) phosphoramidates: amiprofos-methyl, butamifos;
(K1-5) pyridines: dithiopyr, thiazopyr;

K2. Inhibitors of mitosis/microtubule formation (K2-1) carbamates: carbetamide, chlorpropham, propham, swep, karbutilate;

K3. Very long chain fatty acid (VLCFA) inhibitor (cell division inhibitor)
(K3-1) acetamides: diphenamide, napropamide, naproanilide;
(K3-2) Chloroacetamides: acetochlor, alachlor, butachlor, butenachlor, diethatyl-ethyl, dimethachlor, dimethenamid, dimethenamid-P ( dimethenamid-P), metazachlor, metolachlor, pethoxamide, pretilachlor, propachlor, propisochlor, S-metolachlor, thenylchlor;
(K3-3) oxyacetamides: flufenacet, mefenacet;
(K3-4) tetrazolinones: fentrazamide;
(K3-5) Other compounds: anilofos, bromobutide, cafenstrole, indanofan, piperophos, fenoxasulfone, pyroxasulfone, ipfen carbazone (ipfencarbazone);

L. Cellulose synthesis inhibitor (L-1) benzamides: isoxaben;
(L-2) Nitriles: dichlobenil, chlorthiamide;
(L-3) triazolocarboxamides: flupoxame;

M. Uncoupling agent (membrane disrupting agent)
(M-1) Dinitrophenols: dinoterb, DNOC (including salts such as amines and sodium);

N. Lipid biosynthesis inhibitors (excluding ACCase inhibitors)
(N-1) benzofurans: benfuresate, ethofumesate;
(N-2) Halogenated carboxylic acids: dalapon, flupropanate, TCA (trichloroacetic acid) (including salts such as sodium, calcium, ammonia);
(N-3) phosphorodithioates: bensulide;
(N-4) Thiocarbamates: butylate, cycloate, dimepiperate, EPTC, esprocarb, molinate, orbencarb, pebulate, prosulfocarb ( prosulfocarb, thiobencarb, tiocarbazil, tri-allate, vernolate;

O. Synthetic auxin (O-1) benzoic acids: chloramben, 2,3,6-TBA (2,3,6-trichlorobenzoic acid), dicamba (amines, diethylamine, isopropylamine, diglycolamine, including salts of sodium, lithium, etc.);
(O-2) Phenoxycarboxylic acids: 2,4,5-T, 2,4-D (including salts such as amine, diethylamine, triethanolamine, isopropylamine, sodium, lithium), 2,4-DB ( 4-(2,4-dichlorophenoxy)butyric acid), clomeprop, dichlorprop, dichlorprop-P, MCPA ((4-chloro-2-methylphenoxy)acetic acid) , MCPA-thioethyl, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) (including sodium salts, ethyl esters, etc.), mecoprop (sodium, potassium, isopropylamine, triethanolamine, dimethylamine etc.), mecoprop-P;
(O-3) pyridinecarboxylic acids: clopyralid, fluroxypyr, picloram, triclopyr, triclopyr-butotyl, halauxifen-methyl;
(O-4) quinoline carboxylic acids: quinclorac, quinmerac;
(O-5) Other compounds: benazolin;

P. Auxin transport inhibitor (P-1) phthalamates: naptalam (including salts with sodium, etc.);
(P-2) semicarbazones: diflufenzopyr;

Z. Compounds of unknown mechanism of action flamprop-M (including methyl, ethyl and isopropyl esters), flamprop (including methyl, ethyl and isopropyl esters), chlorflurenol-methyl , cinmethylin, cumyluron, daimuron, methyldymuron, difenzoquat, etobenzanid, fosamine, pyributicarb, oxaziclomefone, acrolein , AE-F-150954 (code number), aminocyclopyrachlor, cyanamide, heptamaloxyloglucan, indaziflam, triaziflam, quinoclamine, endothaldi Sodium (endothal-disodium), phenisopham, SL-573 (code number) (1-cyclopropylmethyl-6-methoxy-4-phenyl-2(1H)-quinazolinone), cyclopyrimonate plant Growth regulators: 1-methylcyclopropene, 1-naphthylacetamide, 2,6-diisopropylnaphthalene, 4-CPA ((4-chlorophenoxy)acetic acid), benzylaminopurine, ancymidol, aviglycine , carvone, chlormequat, cloprop, cloxyfonac, cloxyfonac-potassium, cyclanilide, cytokinins, daminozide, dikeglac ( dikegulac), dimethipin, ethephon, ethychlozate, flumetralin (f lumetralin, flurenol, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indoleacetic acid, indolebutyric acid, maleic hydrazide, mefluidide, mepiquat chloride ( mepiquat chloride), n-decanol, paclobutrazol, prohexadione-calcium, prohydrojasmon, sintofen, thidiazuron, triacontanol, trinexapak Ethyl (trinexapac-ethyl), uniconazole, uniconazole-P, 4-oxo-4-(2-phenylethyl) aminobutyric acid (chemical name, CAS registration number: 1083-55-2 )

The following are examples of known safeners that can be mixed or used in combination.

benoxacor, furilazole, dichlormid, dicyclonone, DKA-24 (N1,N2-diallyl-N2-dichloroacetylglycinamide), AD-67 (4-dichloroacetyl-1-oxa -4-azaspiro[4.5]decane), PPG-1292 (2,2-dichloro-N-(1,3-dioxan-2-ylmethyl)-N-(2-propenyl)acetamide), R-29148 ( 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine), cloquintcet-methyl, 1,8-naphthalic anhydride, mefenpyrdiethyl, mefenpyr ), mefenpyr-ethyl, fenchlorazole O ethyl, fenclorim, MG-191 (2-dichloromethyl-2-methyl-1,3-dioxane), siometrinil ( cyometrinil, flurazole, fluxofenim, isoxadifen, isoxadifen-ethyl, mecoprop, MCPA, daimuron, 2,4-D ((2, 4-dichlorophenoxy)acetic acid), MON 4660 (code number) (4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane), oxabetrinil, cyprosulfamide, Lower alkyl-substituted benzoic acid, TI-35 (code number) and N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (chemical name, CAS registry number: 129531-12-0)

The insect pest control agent of the present invention, which is composed as described above, is classified into the order Orthoptera, Thysanoptera, Hemiptera, Coleoptera, Diptera, Lepidoptera, Hymenoptera, Mycophylla, Omiformes, and Roaches. Excellent against insect pests such as , Isoptera, Anthoptera, Cervidae, Louses, plant feeding mites, plant parasitic nematodes, plant parasitic mollusc pests, other crop pests, nuisance pests, sanitary pests, and parasites. It shows the control effect. The following species are examples of such pests.

Orthoptera pests are, for example,
Tettigoniidae: Ruspolia lineosa, etc.
Cricket family (Gryllidae): Emma cricket (Teleogryllus emma), etc.
Gryllotalpidae: Mole cricket (Gryllotalpa orientalis),
Acrididae: grasshopper (Oxya hyla intricate), migratory locust (Locusta migratoria), locust (Melanoplus sanguinipes), etc.
Pyrgomorphidae: Long-tailed locust (Atractomorpha lata),
Eneopteridae: Euscrytus japonicus,
Flea locust family (Tridactylidae): Can be flea locust (Xya japonicus) and the like.

Thysanoptera pests are, for example,
Thripidae: Frankliniella intonsa, Frankliniella occidentalis, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, etc.
Phlaeothripidaes: can be Ponticulothrips diospyrosi, Haplothrips aculeatus, and the like.

Hemiptera pests are, for example,
Cicadidae: Mogannia minuta, etc.
Aphrophoridae: Aphorphora intermedia, etc.
Membracicdae: Tobiirotsunosemi (Machaerotypus sibiricus), etc.
Cicadellidae: Arboridia apicalis, Empoasca onukii, Nephotettix cincticeps, Recilia dorsalis, etc.
Cixiidae: Pentastiridius apicalis, etc.
Planthopper family (Delphacidae): rice planthopper (Laodelphax striatella), brown planthopper (Nilaparvata lugens), green planthopper (Sogatella furcifera), etc.
Meenoplidae: Nisia nervosa, etc.
Derbidae: Kamendaka saccharivora, etc.
Giant planthopper (Cixidia okunii): Red fungus bug (Achilus flammeus), etc.
Ricaniidae: Orosanga japonicus, etc.
Flatidae: Tobiirohagoromo (Mimophantia maritima), etc.
Phylliidae (Psyllidae): pear lice (Cacopsylla pyrisuga), etc.
Calophyidae: Mango lice (Calophya mangiferae), etc.
Phylloxeridae: Grape aphid (Daktulosphaira vitifoliae), etc.
Adelgidae: Adelges laricis, Adelges tsugae, etc.
Aphididae: Acyrthosiphon pisum, Aphis gossypii, Aphis spiraecola, Lipaphis erysimi, Myzus persicae, Schizaphis graminum ), wheat neck aphids (Rhopalosiphum padi), etc.
Aleyrodidae: Aleurocanthus spiniferus, Bemisia tabaci, Bemisia argentifolii, Trialeurodes vaporariorum, etc.
Margarodidae: Drosicha corpulenta, Icerya purchasi, etc.
Pseudococcidae: pineapple mealybug (Dysmicoccus brevipes), mandarin orange mealybug (Planococcus citri), mulberry mealybug (Pseudococcus comstocki), etc.
Coccidae: Ceroplastes ceriferus, etc.
Aclerdidae: Aclerda takahasii, etc.
Diaspididae: Aonidella aurantii, Diaspidiotus perniciosus, Unaspis yanonensis, etc.
Family Miridae: Lygus hesperus, Trigonotylus caelestialium, etc.
Tingidae: Azalea (Stephanitis pyrioides), Nasi Gunbai (Stephanitis nashi), etc.
Pentatomidae: Eysarcoris aeneus, Lagynotomus elongatus, Nezara viridula, Plautia crossota, etc.
Plataspidae: Taiwan Mars stink bug (Megacopta cribaria), etc.
Long stink bug family (Lygaeidae): such as the long stink bug (Cavelerius saccharivorus),
Malcidae family: Malcidae (Malcus japonicus), etc.
Pyrrhocoridae: Dysdercus cingulatus, etc.
Alydidae family (Alydidae): Leptocorisa acuta, Leptocorisa chinensis, etc.
Family (Coreidae): Okumo Helicum Meshi (Anacanthocoris striicornis), etc.
Rhopalidae: Rhopalus maculatus, etc.
Bed Bug family (Cimicidae): can be bed bugs (Cimex lectularis) and the like.

Coleoptera pests are
Scarabaeidae (Scarabaeidae): Anomara cuprea, Anomara rufocuprea, Popillia japonica, Oryctes rhinoceros, etc.
Click beetle family (Elateridae): Agriotes ogurae, Melanotus okinawensis, Melanotos fortnumi fortnumi, etc.
Dermestidae: Himemarukatsuobushimushi (Anthrenus verbasci), etc.
Bostrychidae: Heterobostrychus hamatipennis, etc.
Anobiidae: Stegobium paniceum, etc.
Ptinidae: Pitinus clavipes, etc.
Trigoniaceae (Trogossitidae): Trigum (Tenebroides manritanicus), etc.
Cleridae: Necrobia rufipes,
Nitidulidae: Carpophilus hemipterus, etc.
Family Silvanidae: Ahasverus advena, etc.
Laemophloeidae: Sabikakumune Hiratamushi (Cryptolestes ferrugineus), etc.
Coccinellidae: Coccinellidae: Epilachna varivestis, Henosepilachna vigintioctopunctata, etc.
Tenebrionidae: Tenebrio molitor, Tribolium castaneum, etc.
Blister beetle family (Meloidae): bean tiger beetle (Epicauta gorahami), etc.
Cerambycidae: Anoplophora glabripennis, Xylotrechus pyrrhoderus, Monochamus alternatus, etc.
Bean weevil family (Bruchidae): Azuki weevil (Callosobruchus chinensis), etc.
Chrysomelidae: Colorado potato beetle (Leptinotarsa decemlineata), Western corn rootworm (Diabrotica virgifera), Radish beetle (Phaedon brassicae), Chrysanthemum beetle (Phyllotreta striolata), etc.
Brentidae: Cylas formicarius, etc.
Curculionidae: Alfalfa Octopus Weevil (Hypera postica), Yasai Weevil (Listroderes costirostris), Potato Weevil (Euscepes postfasciatus), etc.
Rice weevil (Erirhinidae): rice weevil (Echinocnemus bipunctatus), rice water weevil (Lissorhoptrus oryzophilus), etc.
Dryophthoridae: Sitophilus zeamais, Sphenophrus venatus, etc.
Scolytidae: Pine bark beetle (Tomicus piniperda), etc.
Platypodidae: Crossotarsus niponicus, etc.
Lyctidae: Can be Lyctus brunneus and the like.

Diptera pests are, for example,
Crane family (Tipulidae): Tipila aino, etc.
Bibionidae: love bug (Plecia nearctica), etc.
Family Mycetophidae: Exechia shiitakevora, etc.
Sciaridae: potato flies (Pnyxia scabiei), etc.
Cecidomyiidae: Asphondylia yushimai, Mayetiola destructor, etc.
Culicidae: Aedes aegypti, Culex pipiens pallens, etc.
Family: Simuliidae: Simulim takahasii, etc.
Chironomidae (Chironomidae): rice chironomid (Chironomus oryzae), etc.
Tabanidae: Chrysops suavis, Tabanus trigonus, etc.
Hanafidae (Syrphidae): Heidi Mahanaf (Eumerus strigatus), etc.
Family Tephritidae: Bactrocera dorsalis, Euphranta japonia, Ceratitis capitata, etc.
Agromyzidae: Liriomyza trifolii, Chromatomyia horticola, etc.
Chloropidae: Meromyza nigriventris, etc.
Drosophilidae: Drosophila suzukii, Drosophila melanogaster, etc.
Ephydridae: Hydrellia griseola, etc.
Hippoboscidae: Hippobosca equina, etc.
Scatophagidae: Parallelpmma sasakawae, etc.
Anthomyiidae: onion fly (Delia antiqua), seed fly (Delia platura), etc.
Fanniidae: Fannia canicularis, etc.
Housefly family (Muscidae): Musca domestica, stable fly (Stomoxys calcitrans), etc.
Sarcophagidae: Sarcophaga peregrina, etc.
Gasterophilidae: Gasterophilus intestinali, etc.
Hypodermatidae: Hypoderma lineatum, etc.
Oestridae: can be Oestrus ovi and the like.

Lepidopteran pests are, for example,
Bat moth (Hepialidae): Bat moth (Endoclita excrescens), etc.
Heliozelidae: Antispila ampelopsia, etc.
Cossidae: Zeuzera leuconotum, etc.
Tortricidae: Archips fuscocupreanus, Adoxophyes orana fasciata, Grapholita molesta, Homona magnanima, Legumivora glycinivorella, Cydia pomonella, etc.
Cochylidae: Eupoecilia ambiguella, etc.
Family Psychidae: Bambalina sp., Eumeta minuscula, etc.
Tineidae: small moth (Nemapogon granella), burr (Tinea translucens), etc.
Bucculatricidae: Bucculatrix pyrivorella, etc.
Lyonetiidae: Lyonetia clerkella, etc.
Family Gracilariidae: Chanohamakihosogha (Caloptilia theivora), Kinmonhosogha (Phyllonorycter ringoniella), etc.
Phyllocnistidae: Phyllocnistis citrella, etc.
Acrolepiidae: Acrolepiopsis sapporensis, etc.
Saga family (Yponomeutidae): Diamondback moth (Plutella xylostella), Ring moth (Yponomeuta orientalis), etc.
Subfamily Argyrestidae: Argyrestia conjugella, etc.
Family Sesidae: Nokona regalis, etc.
Gelechiidae: Phthorimaea operculella, Sitotroga cerealella, Pectinophora gossypiella, etc.
Carposinidae: Peach moth (Carposina sasakii), etc.
Zygaenidae: Illiberis pruni, etc.
Limacodidae: Monema flavescens, etc.
Crambidae family: Tsutoga (Ancylolomia japonica), Nikameiga (Chilo suppressalis), Kobunomeiga (Cnaphalocrosis medinalis), Cornflower (Ostrinia furnacalis), Cornflower (Ostrinia nubilalis), etc.
Pyralidae (Pyralidae): Cadra cautella, Galleria mellonella, etc.
Pterophoridae: Nippoptilia vitis, etc.
Papilionidae: Papilio xuthus, etc.
Pieridae: Pieris rapae, etc.
Hesperiidae (Hesperiidae): Parnara guttata guttata, etc.
Geometridae: Ascotis selenaria, etc.
Family (Lasiocampidae): Matsukareha (Dendrolimus spectabilis), Obikareha (Malacosomaneustrium testaceum), etc.
Sphingidae: Shrimp sparrow (Agrius convolvuli), etc.
Lymantriidae: Chadokuga (Arna pseudoconspersa), gypsy moth (Lymantria dispar), etc.
Arctiidae: Hyphantria cunea, etc.
Noctuidae: Agrotis ipsilon, Autographa nigrisigna, Helicoverpa armigera, Helicoverpa zea, Heliothis virescens, Spodoptera exigua, Lotus Spodoptera litura) and the like.

Hymenoptera pests are, for example,
Argidae: Arge pagana, etc.
Sawfly family (Tenthredinidae): chestnut sawfly (Apethymus kuri), turnip sawfly (Athalia rosae ruficornis), etc.
Cynipidae: Dryocosmus kuriphilus, etc.
Vespidae: Vespa simillima xanthoptera, etc.
Formicidae: Fire ants (Solenopsis invicta), etc.
Megachilidae: Can be Megachile nipponica and the like.

Pests of the order Myxochoda, for example,
Family Sminthuridae: Can be Bourletiella hortensis and the like.

Examples of pests of the order Amphiprae are
Lepismatidae: can be Lepisma saccharina, Ctenolepisma villosa, and the like.

Examples of cockroach pests include:
Cockroach family (Blattidae): American cockroach (Periplaneta americana),
Blattellidae: can be Blattella germanica and the like.

Examples of isoptera pests include:
Kalotermitidae: American Kanzai termites (Incisitermes minor), etc.
Rhinotermitidae: Formosan termites (Coptotermes formosanus), etc.
Termitidae: Can be Odontotermes formosanus and the like.

Examples of insect pests of the Order Bookworm include:
Trogiidae: Trogium pulsatorium, etc.
Liposcelididae: can be Liposcelis corrodens and the like.

Examples of pests of the order Aphidae include:
Menoponidae: Chick longhead louse (Lipeurus caponis), etc.
Trichodectidae: can be bovine lice (Damalinia bovis) and the like.

Examples of pediculoid pests are:
Haematopinidae: Pig lice (Haematopinus suis), etc.
Pediculine: head lice (Pediculus humanus), etc.
Linognathidae: Canine lice (Linognathus setosus), etc.
Pthiridae: Can be Phthrius pubis and the like.

Examples of plant-eating mite pests include:
Eupodidae: Penthaleus major, etc.
Tarsonemidae: Phytonemus pallidus, Polyphagotarsonemus latus, etc.
Pyemotidae: Pyemotidae (Siteroptes sp.), etc.
Tenuipalpidae: Grape spider mite (Brevipalpus lewisi), etc.
Tuckerellidae: Tuckerella pavoniformis, etc.
Tetranychidae: Eotetranychus boreus, Panonychus citri, Panonychus ulmi, Tetranychus urticae, Tetranychus kanzawai, etc.
Nalepellidae: Trisetacus pini, etc.
Eriophyidae: Aculops pelekassi, Epitrimerus pyri, Phyllocoptruta oleivola, etc.
Diptilomiopidae: Diptacus crenatae, etc.
Acaridae: can be Aleuroglyphus ovatus, Tyrophagus putrescentiae, Rhizoglyphus robini, and the like.

Examples of plant parasitic nematode pests include:
Longidoridae: Grape Nematodes (Xiphinema index), etc.
Trichodoridae (Trichodoridae): such as Paratrichodorus minor,
Rhabditidae: Rhabditella sp.
Porcupine family (Tylenchidae): Aglenchus species (Aglenchus sp.), etc.
Tylodoridae: Cephalenchus sp.
Anguinidae: Strawberry nematode (Nothotylenchus acris), Imogusare nematode (Ditylenchus destructor), etc.
Spear nematode (Hoplolaimidae): Rotylenchus reniformis, Namira nematode (Helicotylenchus dihystera), etc.
Paratylenchidae: Paratylenchus curvitatus, etc.
Meloidogyne family (Meloidogynidae): Meloidogyne incognita, Meloidogyne hapla, etc.
Family Heteroderidae: Globodera rostochiensis, Heterodera glycines, etc.
Telotylenchidae: Tylenchorhynchus claytoni, etc.
Psilenchus family (Psilenchidae): Psilenchus species (Psilenchus sp.), etc.
Criconematidae: Criconemoides sp.
Tylenchulidae: Tylenchulus semipenetrans, etc.
Spaeronematidae: Sphaeronema camelliae, etc.
Platylenchidae: Sphaeronema camelliae, Radopholus citrophilus, Radopholus similis, Nacobbus aberrans, Pratylenchus penetrans, Minami Negusare nematodes (Pratylenchus coffeeae), etc.
Iotonchiidae: Iotonchium ungulatum, etc.
Aphelenchidae: Aphelenchus avenae, etc.
Aphelenchoidea (Aphelenchoididae): rice nematode (Aphelenchoides besseyi), strawberry nematode (Aphelenchoides fragariae), etc.
Palasitaphelenchidae: Can be Bursaphelenchus xylophilus and the like.

Examples of plant parasitic mollusc pests are
Pilidae: Pomacea canaliculata, etc.
Veronicellidae: Leavicaulis alte, etc.
African snail (Achatinidae): African snail (Achatina fulica), etc.
Slug family (Philomycidae): slugs (Meghimatium bilineatum), etc.
Succineidae: Succinea lauta, etc.
Family: Didcidae: Discus pauper, etc.
Zonitidae: Zonitoides yessoensis, etc.
Limacidae: Limax flavus, Deroceras reticulatum, etc.
Helicarionidae: Parakaliella harimensis, etc.
Bradybaenidae: can be Acusta despecta sieboldiana, Bradybaena similaris, and the like.

Other pests such as harmful animals, nuisance animals, sanitary insects, livestock insects, parasites, etc.
Acari Macronysshidae: Ornithonyssus sylvialum, etc.
Varroidae: Varroa jacobsoni, etc.
Dermanyssidae: red mites (Dermanyssus gallinae), etc.
Macronyssidae: Ornithonyssus sylvialum, etc.
Ixodidae: Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, etc.
Sacroptidae: Sarcoptes scabiei, etc.
Isopoda Armadillididae: Armadillidium vulgare, etc.
Decapoda Astacidae: American crayfish (Procambarus clarkii), etc.
Porcellionidae: Armadillidium vulgare, etc.
Centipede pests (Chilopoda pests): Scutigeromorpha Sutigeridae, Thereuonema tuberculata, Scolopendromorpha Scolopendra subpinipes, etc.
Diplopoda pests: Polydesmida Paradoxosomatidae Oxidus gracillis, etc.
Araneae Redback spider family (Araneae Latrodectus hasseltii): Redback spider (Theridiiadae hasseltii), etc.
Family of spiders (Clubionidae): Chiracanthium japonicum, etc.
Order Scorpionida: Sinai Desert Scorpion (Androctonus crassicauda), etc.
Parasitic roundworms: Ascaris lumbricoides, Syphacia sp., Wucherebia bancrofti, etc.
Parasitic flatworms: Distomum sp., Paragonimus westermanii, Metagonimus yokokawai, Schistosoma japonicum, Taenia solium, no It can be Taeniarhynchus saginatus, Echinococcus sp., Diphyllobothrium latum, and the like.

In addition, the present pest control agent exhibits control effects against the above-mentioned pests and the like that are already resistant to existing pest control agents. Furthermore, the present control agent can be applied to plants already resistant to insects, diseases, herbicides, etc. by genetic modification, artificial mating, or the like.

Next, the manufacturing method, formulation method and application of the present compound will be described in detail in the form of examples. However, the invention is not limited merely by these examples.

In addition, methods for producing intermediates for producing the present compound are also described.

The present invention will be described in more detail with reference to the following preparation examples, formulation examples and test examples. However, the present invention is not limited to these examples. Also, modifications can be made without departing from the scope of the present invention.

Preparation example 1
Preparation of 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(trifluoromethyl)isoxazole (compound 1) (1) 4, 4,4-trifluoro-1-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)butane-1,3-dione 1-(5-(2 ,2,2-trifluoroethylthio)-2-fluoro-4-methylphenyl)ethanone (10.0 g, 37.0 mmol) in THF (100 mL) was added with NaH (60% in mineral oil, 2.20 g, 55.0 mmol) was added in three portions while maintaining the temperature between 0-10°C. After stirring for 20 minutes at this temperature, ethyl trifluoroacetate (7.88 g, 55.0 mmol) was slowly added. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was then poured into ice water, acidified with 2M HCl solution and extracted with ethyl acetate (3×100 mL). The combined organic layers were then washed with distilled water (2 x 100 mL), dried over sodium sulfate and concentrated under reduced pressure to give crude product (14.0 g). The crude product thus obtained was used further without any purification.
¹ H NMR (CDCl ₃ ): 8.13 (d, J = 6.8 Hz, 1H), 7.09 (d, J = 12.4 Hz, 1H), 6.68 (m, 1H), 3.39 (q, J = 9.6 Hz, 2H) , 2.54 (s, 3H).

(2) 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-5 -ol 4,4,4-trifluoro-1-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)butane-1,3-dione (1. 0 g, 2.70 mmol) in ethanol (25 mL) was added hydroxylamine hydrochloride (0.29 g, 4.10 mmol) at 10°C. The mixture was then stirred at 80° C. for 3 hours. After distillation of ethanol, the residue was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The residue was then purified by column chromatography (ethyl acetate:n-hexane=1:2) to give 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl )thio)phenyl)5-(trifluoromethyl)-4,5-dihydroisoxazol-5-ol (0.45 g, 43.2% yield).
¹ H NMR (CDCl ₃ ): 8.05 (d, J = 7.2 Hz, 1H), 7.05 (d, J = 11.6 Hz, 1H), 3.75-3.80 (m, 1H), 3.55-3.63 (m, 1H), 3.38 (q, J = 9.6 Hz, 2H), 2.51 (s, 3H).

(3) 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(trifluoromethyl)isoxazole (compound 1)
3-(2-fluoro-4-methyl-5-(((2,2,2-trifluoroethyl)thio)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-5-ol (6.50 g, 17.0 mmol) in toluene (80 mL) was added thionyl chloride (3.07 g, 26.0 mmol) and pyridine (5.36 g, 68.0 mmol) at room temperature. , 100 ^° C. for 1 hour After cooling to room temperature, the reaction mixture was extracted with dichloromethane (3×100 mL) The combined organic layers were then washed with brine, dried over sodium sulfate, After filtration and concentration under reduced pressure, the residue was purified by column chromatography (ethyl acetate:n-hexane=1:4) to give 3-(2-fluoro-4-methyl-5-(( 2,2,2-Trifluoroethyl)thio)phenyl)-5-(trifluoromethyl)isoxazole (6.10 g, 98.5% yield) was obtained.
1H NMR ( _CDCl3 ): 8.18 (d, J = 7.2 Hz, 1H), ^7.11-7.14 (m, 2H), 3.40 (q, J = 9.6 Hz, 2H), 2.54 (s, 3H).

Preparation example 2
Preparation of 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole (Compound 37) ( 1) 2-fluoro-N-methoxy-N,4-dimethylbenzamide To a solution of 2-fluoro-4-methylbenzoic acid (20.0 g, 130 mmol) in dichloromethane (200 mL) was added N,O-dimethylhydroxylamine (18. 9 g, 190 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (37.3 g, 190 mmol), 1-hydroxybenzotriazole hydrate (26.3 g, 190 mmol) and diisopropylethylamine (72 mL, 390 mmol) was added at 0°C. The reaction mixture was then stirred at room temperature for 1 hour. The reaction mixture was then poured into ice water and extracted with ethyl acetate (3x100ml). The combined organic layers were then washed with distilled water (2 x 100 mL), dried over sodium sulfate and concentrated under reduced pressure to give crude product (22.0 g, 86%). The crude product thus obtained was used further without any purification.
¹ H NMR (CDCl ₃ ): 7.32 (t, J = 7.6 Hz, 1H), 6.99 (d, J = 7.6 Hz, 1H), 6.91 (d, J = 10.8 Hz, 1H), 3.57 (s, 3H) , 3.33 (s, 3H), 2.37 (s, 3H).

(2) 1-(2-fluoro-4-methylphenyl)propan-1-one 2-fluoro-N-methoxy-N,4-dimethylbenzamide (8.0 g, 40.0 mmol) in anhydrous THF (150 ml) To the solution was added ethylmagnesium bromide (80 mL, 80.0 mmol, 1 M solution in THF) dropwise at 0.degree. The reaction mixture was then stirred at room temperature for 3 hours. The reaction mixture was then poured into ice water and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were then washed with distilled water (2 x 100 mL), dried over sodium sulfate and concentrated under reduced pressure to give crude product (3.20 g, 48%). The crude product thus obtained was used further without any purification.
¹ H NMR (CDCl ₃ ): 7.78 (t, J = 8.0 Hz, 1H), 7.02 (d, J = 8.0 Hz, 1H), 6.93 (d, J = 12 Hz, 1H), 2.94-2.99 (m, 2H), 1.19 (t, J = 7.2 Hz, 3H).

(3) 4,4,4-trifluoro-1-(2-fluoro-4-methylphenyl)-2-methylbutane-1,3-dione 1-(2-fluoro-4-methylphenyl)propane-1- To ON (5.0 g, 30.0 mmol) in anhydrous THF (60 mL) was added lithium bis(trifluoromethylsilyl)amide (7.5 g, 45.0 mmol) dropwise at -20°C. After stirring for 30 minutes at this temperature, ethyl trifluoroacetate (6.41 g, 45.0 mmol) was added slowly at -20°C. The reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was then poured into ice water, acidified with 2M HCl solution and extracted with ethyl acetate (3×80 ml). The combined organic layers were then washed with distilled water (2 x 50 mL), dried over sodium sulfate and concentrated under reduced pressure to give crude product (7.2 g). The crude product thus obtained was used further without any purification (377 (M+H), 46% purity by LC-MS).

(4) 3-(2-fluoro-4-methylphenyl)-4-methyl-5-(trifluoromethyl)-4,5-dihydroisoxazol-5-ol 4,4,4-trifluoro-1- To a solution of (2-fluoro-4-methylphenyl)-2-methylbutane-1,3-dione (7.2 g, 27.0 mmol) in ethanol (50 mL) was added hydroxylamine hydrochloride (3.81 g, 54.0 mmol). was added at room temperature. The mixture was then refluxed at 80° C. for 3 hours. After distillation of ethanol, the residue was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The residue was then purified by chromatography (ethyl acetate:n-hexane=1:1) to give 3-(2-fluoro-4-methylphenyl)-4-methyl-5-(trifluoromethyl)- 4,5-dihydroisoxazol-5-ol (3.0 g, 39% yield) was obtained.
¹ H NMR (CDCl ₃ ): 7.55 (t, J = 8.0 Hz, 1H), 7.30 (d, J = 8.0 Hz, 1H), 6.98 (d, J = 12.4 Hz, 1H), 3.98-4.07 (m, 1H), 3.32 (bs, 1H), 2.40 (s, 3H), 1.26 (d, J = 7.6 Hz, 3H).

(5) 3-(2-fluoro-4-methylphenyl)-4-methyl-4-methyl-5-(trifluoromethyl)isoxazole 3-(2-fluoro-4-methylphenyl)-4-methyl under N ₂ To a solution of 5-(trifluoromethyl)-4,5-dihydroisoxazol-5-ol (3.0 g, 10.8 mmol) in toluene (20 mL) was added thionyl chloride (2.03 g, 16.2 mmol) and pyridine. (6.61 g, 54.0 mmol) was added at 0°C. The mixture was then heated at 100° C. for 1 hour. After cooling to room temperature, the reaction mixture was extracted with dichloromethane (3 x 80 mL). The combined organic layers were then washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was then purified by chromatography (ethyl acetate:n-hexane=1:4) to give 3-(2-fluoro-4-methylphenyl)-4-methyl-5-(trifluoromethyl)iso Oxazole (2.0 g, 71% yield) was obtained.
¹ H NMR (CDCl ₃ ): 7.39 (t, J = 7.6 Hz, 1H), 7.09 (d, J = 7.6 Hz, 1H), 7.04 (d, J = 10.8 Hz, 1H), 2.43 (s, 3H) , 2.13 (t, J = 2.0 Hz, 3H).

(6) 4-fluoro-2-methyl-5-(4-methyl-5-(trifluoromethyl)isoxazol-3-yl)benzenesulfonyl chloride chlorosulfonic acid (4.49 g, 38.6 mmol) was added to the reaction Slowly added to 3-(2-fluoro-4-methylphenyl)-4-methyl-5-(trifluoromethyl)isoxazole (2.0 g, 7.71 mmol) keeping the temperature of the mixture below 30°C. . The resulting mixture was then heated to 70° C. for 4 hours. After cooling to room temperature, the reaction mixture was then carefully poured into ice. The precipitate was filtered, washed thoroughly with distilled water and dried to give 0.80 g of crude product. The crude product thus obtained was used further without any purification.
¹ H NMR (CDCl ₃ ): 8.30 (d, J = 6.8 Hz, 1H), 7.32 (d, J = 10 Hz, 1H), 2.88 (s, 3H), 2.16 (t, J = 2.0 Hz, 3H) .

(7) 4-fluoro-2-methyl-5-(4-methyl-5-(trifluoromethyl)isoxazol-3-yl)benzenethiol 4-fluoro-2-methyl-5- in toluene (20 mL) To a stirred solution of (4-methyl-5-(trifluoromethyl)isoxazol-3-yl)benzenesulfonyl chloride (0.80 g, 2.23 mmol) was added triphenylphosphine (2.34 g, 8.90 mmol) in N ₂ was added at 0°C. The reaction mixture was then heated at 100° C. for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature and then 1N NaOH solution (20 ml) was added. After layer separation, the aqueous layer was washed with ethyl acetate (3 x 50 mL). The aqueous layer was then acidified with 6N HCl solution (30 mL). The resulting precipitate was collected by filtration, washed with distilled water (3 x 50 mL) and dried under vacuum to give the title product as a white solid (0.16 g, 22% yield). The crude product thus obtained was used further without any purification.
¹ H NMR (CDCl ₃ ): 7.44 (d, J = 6.8 Hz, 1H), 7.07 (d, J = 10.4 Hz, 1H), 3.49 (s, 1H), 2.41 (s, 3H), 2.13 (t, J = 2.0Hz, 3H).

(8) 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole (compound 37)
A solution of 4-fluoro-2-methyl-5-(4-methyl-5-(trifluoromethyl)isoxazol-3-yl)benzenethiol (0.140 g, 0.48 mmol) in dimethylformamide (4 mL) was Cooled to ^oC . To this was added potassium carbonate (0.10 g, 0.72 mmol) and trifluoroethyl iodide (0.201 g, 0.96 mmol) successively. The resulting mixture was then stirred at room temperature for 6 hours. The reaction mixture was then poured into distilled water and extracted with dichloromethane (3 x 25 mL). The combined organic layers were washed with distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The residue was then purified by column chromatography (ethyl acetate:n-hexane=1:5) to give 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl )thio)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole (0.082 g, 45.7% yield).
¹ H NMR (CDCl ₃ ): 7.67 (d, J = 7.2 Hz, 1H), 7.14 (d, J = 10.4 Hz, 1H), 3.37 (q, J = 9.2 Hz, 2H), 2.56 (s, 3H) , 2.13 (t, J = 2.0 Hz, 3H).

Preparation example 3
Preparation of 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole (compound 2) m-CPBA (purity 70%, 4.19 g, 17.0 mmol) of 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5 in dichloromethane (70 mL). Added to a solution of -(trifluoromethyl)isoxazole (6.10 g, 17.0 mmol) at -5 to 0°C. The reaction mixture was stirred at −5 to 10° C. for 30 minutes and then quenched with saturated NaHCO ₃ solution (70 mL). The layers were separated and the aqueous fraction was extracted with dichloromethane (3 x 75 mL). The combined organic layers were washed with saturated NaHCO ₃ solution (2×50 mL) and dried over sodium sulfate. Solvent was removed under reduced pressure. The residue was then purified by column chromatography (ethyl acetate:n-hexane=1:1) to give 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl )sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole (6.0 g, 94.3% yield) was obtained as a white solid.
1H NMR ( _CDCl3 ): 8.61 (d, J = 7.2 Hz, 1H), ^7.15-7.19 (m, 2H), 3.43-3.55 (m, 2H), 2.84 (s, 3H).

Preparation example 4
Preparation of 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfonyl)phenyl)-5-(trifluoromethyl)isoxazole (compound 3) m-CPBA (purity 70%, 0.208 g, 0.84 mmol) of 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5 in dichloromethane (5 mL). Added to a solution of -(trifluoromethyl)isoxazole (0.100 g, 0.28 mmol) at -5 to 0°C. The reaction mixture was stirred at room temperature for 24 hours and then quenched with saturated NaHCO ₃ solution (10 mL). The layers were separated and the aqueous fraction was extracted with dichloromethane (3 x 25 mL). The combined organic layers were washed with saturated NaHCO ₃ solution (2×20 mL) and dried over sodium sulfate. Solvent was removed under reduced pressure. The residue was then purified by column chromatography (dichloromethane:n-hexane=1:1) to give 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) Sulfonyl)phenyl)-5-(trifluoromethyl)isoxazole (0.053 g, 49% yield) was obtained as a white solid.
¹ H NMR (CDCl ₃ ): 8.73 (d, J = 7.2 Hz, 1H), 7.26-7.28 (m, 1H), 7.16 (d, J = 2.8 Hz, 1H), 3.97 (q, J = 8.8 Hz, 2H), 2.78 (s, 3H).

Preparation example 5
Preparation of 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(trifluoromethyl)isoxazole (Compound 22) (1) 4- Chloro-2-methyl-5-(5-(trifluoromethyl)isoxazol-3-yl)benzenesulfonyl chloride Chlorosulfonic acid (11.1 g, 95.5 mmol) was added keeping the temperature of the reaction mixture below 30°C. was slowly added to 3-(2-chloro-4-methylphenyl)-5-(trifluoromethyl)isoxazole (5.0 g, 19.1 mmol) while stirring. The resulting mixture was then heated to 80° C. for 18 hours. After cooling to room temperature, the reaction mixture was then carefully poured onto ice and the precipitate was filtered, washed thoroughly with distilled water and dried to give 6.1 g of crude product. The crude product thus obtained was used further without any purification.
^1H NMR ( _CDCl3 ): 8.48 (s, 1H), 7.63 (s, 1H), 7.21 (s, 1H), 2.84 (s, 3H).

(2) 4-chloro-2-methyl-5-(5-(trifluoromethyl)isoxazol-3-yl)benzenethiol 4-chloro-2-methyl-5-(5-(5-chloro-2-methyl) in glacial acetic acid (60 mL) Zinc dust (5.5 g, 84.5 mmol) was added portionwise to a mixture of (trifluoromethyl)isoxazol-3-yl)benzenesulfonyl chloride (6.1 g, 16.9 mmol) at room temperature. The resulting mixture was then refluxed for 4 hours. After cooling to room temperature, the reaction mixture was diluted with distilled water and ethyl acetate and filtered through a celite bed. The organic layer was thoroughly washed with distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 3.89 g of crude product as a pale yellow solid. The crude product thus obtained was used further without any purification.
^1H NMR ( _CDCl3 ): 7.69 (s, 1H), 7.32 (s, 1H), 7.19 (s, 1H), 3.43 (s, 1H), 2.37 (s, 3H).

(3) 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(trifluoromethyl)isoxazole (Compound 22)
A solution of 4-chloro-2-methyl-5-(5-(trifluoromethyl)isoxazol-3-yl)benzenethiol (3.89 g, 13.2 mmol) in dimethylformamide (20 mL) was cooled to 0°C. . Potassium carbonate (2.7 g, 19.8 mmol) and trifluoroethyl iodide (5.3 g, 19.8 mmol) were added successively to the cooled solution. The resulting mixture was then stirred at room temperature for 6 hours. The reaction mixture was then poured into distilled water and extracted with dichloromethane (3 x 25 mL). The combined organic layers were washed with distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give crude product. The residue was then purified by column chromatography (ethyl acetate:n-hexane=1:5) to give 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl) Thio)phenyl)-5-(trifluoromethyl)isoxazole (3.90 g, 78.8% yield) was obtained.
^1H NMR ( _CDCl3 ): 7.87 (s, 1H), 7.40 (s, 1H), 7.12 (s, 1H), 3.44 (q, J = 9.6 Hz, 2H), 2.50 (s, 3H).

Preparation example 6
Preparation of 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole (Compound 23) m-CPBA (purity 65%, 0.212 g, 0.798 mmol) of 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5 in dichloromethane (25 mL). Added to a solution of -(trifluoromethyl)isoxazole (0.300 g, 0.798 mmol) at -5 to 0°C. The reaction mixture was stirred at −5 to 10° C. for 30 minutes and then quenched with saturated NaHCO ₃ solution (70 mL). The layers were separated and the aqueous fraction was extracted with dichloromethane (3 x 25 mL). The combined organic layers were washed with saturated NaHCO ₃ solution (2×50 mL) and dried over sodium sulfate. Solvent was removed under reduced pressure. The residue was then purified by column chromatography (ethyl acetate:n-hexane=1:1) to give 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl )sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole (0.280 g, 90.0% yield) was obtained as a white solid.
^1H NMR ( _CDCl3 ): 8.34 (s, 1H), 7.47 (s, 1H), 7.10 (s, 1H), 3.40-3.52 (m, 2H), 2.46 (s, 3H).

Representative compounds of the present invention are exemplified in Table 1 below, but the present invention is not limited to these compounds.

The compounds shown in Table 1, other than those obtained in Preparations 1-6, were prepared by methods analogous to those described in Preparations 1-6 or by methods described in the detailed description.

Abbreviations in Table 1 are as indicated below.
F: fluoro, Cl: chloro, Me: _methyl , _CF3 : _{trifluoromethyl , CF2CF3} : _{pentafluoroethyl , CF2CF2CF3} : heptafluoropropyl, _CF2CF2CF2CF3 : _nonafluoro Butyl, _CHF2 : difluoromethyl, _CF2Cl : chlorodifluoromethyl, Ph: phenyl, _CF2Ph : difluoro(phenyl)methyl.

Formulation Example 1: Emulsion 10 parts of each compound of the present invention is dissolved in 45 parts of Solvesso (registered trademark) 150 and 35 parts of N-methylpyrrolidone, and an emulsifier (trade name: Sorpol (registered trademark) 3005X, Toho Chemical (manufactured by Kogyo Co., Ltd.) was added. The mixture was mixed by stirring to obtain a 10% emulsion.

Formulation Example 2: Wettable powder 20 parts of each compound of the present invention was added to a mixture of 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of fine powder of synthetic hydrated silicon dioxide and 54 parts of clay. This mixture was mixed by stirring in a juice mixer to obtain a 20% wettable powder.

Formulation Example 3: Granules 2 parts of sodium dodecylbenzenesulfonate, 10 parts of bentonite and 83 parts of clay are added to 5 parts of each compound of the invention. Each mixture was thoroughly mixed by stirring. An appropriate amount of water was added to this. The resulting mixture was further stirred and granulated with a granulator. The granules were air dried to give 5% granules.

Formulation Example 4: Powder 1 part of each compound of the present invention was dissolved in an appropriate amount of acetone. To this was added 5 parts of a fine powder of synthetic hydrated silicon dioxide, 0.3 parts of isopropyl acid phosphate (PAP) and 93.7 parts of clay. The mixture was mixed by stirring with a juice mixer. Acetone was removed by evaporation to give a 1% powder.

Formulation Example 5: Flowable agent 20 parts of each compound of the present invention was mixed with 20 parts of water containing 3 parts of polyoxyethylene tristyrylphenyl ether phosphate triethanolamine and 0.2 parts of Rhodorsil® 426R. . This mixture was subjected to wet milling in a DYNO-Mill and mixed with 60 parts water containing 8 parts propylene glycol and 0.32 parts xanthan gum to give a 20% suspension in water.

Test examples are provided below to demonstrate that the compounds of the present invention are useful as active ingredients in acaricides and nematicides.

Compound A was a representative compound referred to in the specification of JP-A-2008-308448. This compound A is [I-Ib] No. It was the same as the compound of 2-1.

Test Example 1 (acaricidal test of two-spotted spider mite)
A piece of nonwoven fabric (4.5 x 5.5 cm) was hung inside the plastic cup through a cut made in the lid of the plastic cup. After pouring water into this cup, the cup was covered with a lid. Kidney bean leaves (approximately 3.5 x 4.5 cm) were then placed on the thoroughly soaked nonwoven fabric. Another kidney bean leaf with two-spotted spider mites (approximately 30 mite samples) was placed on top of the first leaf and the cloth and leaf were placed in a constant temperature bath with a temperature of 25±2° C. and a humidity of 40% overnight. placed. The next morning the upper leaves were removed as the mite population had already migrated to the lower leaves.

Acaricidal formulations (100 ppm and 5 ppm) containing a compound of the invention were prepared by adding an aqueous solution (100 ppm) of Sorpol 355 (manufactured by Toho Chemical Industry Co., Ltd.) to a methanol solution of the compound of the invention.

These acaricidal formulations were sprayed on the leaves, which were air-dried and placed in a constant temperature bath (25±2° C. and 50% humidity). After 2 days, two-spotted spider mite mortality was calculated. The results of this test are shown in Table 3.

The compounds (from Table 3) that showed 100% mortality at 5 ppm are:
Compound numbers: 2, 8, 19, 23, 35, 38, 43, 44, 55 and 56.

Test Example 2 (Two-spotted spider mite ovicidal test)
A piece of nonwoven fabric (4.5 x 5.5 cm) was hung inside the plastic cup through a cut made in the lid of the plastic cup. After pouring water into this cup, the cup was covered with a lid. Kidney bean leaves (approximately 3.5 x 4.5 cm) were then placed on the thoroughly soaked nonwoven fabric. Twenty adult female two-spotted spider mites were placed on the leaves and the cloth and leaves were placed overnight in a constant temperature bath with a temperature of 25±2° C. and a humidity of 40% and 16L8D.

The next day, after adjusting the number of adult female insects to 20 again, 2 mL of the acaricidal preparation (10 ppm) containing the compound of the present invention prepared in the same manner as in Test Example 1 was sprayed on the leaves, and the leaves were air-dried. Placed in a constant temperature bath (25±2° C. and 50% humidity). Two-spotted spider mite ovicidal rate was calculated 6 days after spraying with the acaricidal formulation. The results of this test are shown in Table 4.

Compounds (from Table 4) that showed 100% mortality at 10 ppm are:
Compound numbers: 2, 17, 19, 23, 35, 38, 43, 44, 55 and 56.

The compounds (from Tables 3 and 4) that showed 100% mortality at 5 ppm in Table 3 and 100% mortality at 10 ppm in Table 4 are:
Compound numbers: 2, 19, 23, 35, 38, 43, 44, 55 and 56.

Test Example 3 (acaricidal test of two-spotted spider mites (systemic activity))
10 mL of test compound solution is added to 8-day-old kidney bean pots (6.5 cm diameter and 6.5 cm height) at 10 mg a. i. / Irrigate in pots. After application the plants are placed in a greenhouse at a temperature of 25±2°C. After 5 days, kidney bean leaves (approximately 3.5 x 4.5 cm) from the treated pots were placed on the thoroughly soaked non-woven fabric. Two-spotted spider mites (approximately 30 tick samples) were placed on the leaves and the cups were placed in a constant temperature bath with a temperature of 25±2°C. After 2 days, adult two-spotted spider mite mortality was calculated. Compounds showing 50% or more mortality are as follows.
Compound numbers: 2, 16, 17, 23, 35, 43, 44 and 49.

Test Example 4 (Nematicidal test of root-knot nematode)
1 mL of test compound with desired concentration (40 ppm) and 1 mL of nematode suspension (500 nematodes/mL) were added to a wide mouth glass vial filled 2/3 with sea sand (8 g). The mouth of the vial was sealed with stretch parafilm and pierced in the center. Two to three week old tomato plants were cut from the stems and inserted into test vials. The vials were kept in a constant temperature bath with a temperature of 25±2°C. After two weeks, the plants were carefully removed from the vials and evaluated for root-knot nodules. The rating was based on a score of 0-4 (0 is no infestation; 4 is 100% infestation). The degree of nodule damage was determined according to the index shown in Table 5.

The compounds that showed a nodule index of 1 or less were as follows.
Compound numbers: 2, 5, 9, 10, 13, 14, 17, 19, 20, 23, 25, 27, 29, 31, 35, 38, 40, 43, 44, 46, 49, 50, 55 and 56 .

(Note)
Above, the present invention has been illustrated by the preferred embodiments of the present invention. However, it will be understood that the scope of the invention should be construed only by the claims that follow. It is understood that the patents, patent applications and publications cited herein are hereby incorporated by reference as if their contents were specifically set forth herein. This application claims priority to Indian Patent Application No. 201711042933 filed on November 30, 2017 with Intellectual Property India, the entire contents of which are incorporated herein by reference. .

The isoxazole compounds of the present invention exhibit excellent control effects against a wide range of insect pests, such as mites and plant parasitic nematodes, and are useful as agricultural and horticultural acaricides or nematicides.

Claims (7)

Formula (I):

[In the formula, R is normal propyl or 2,2,2-trifluoroethyl.
A. ¹ and A ² is fluorine, chlorine or methyl.
B. ¹ is hydrogen or methyl.
B. ² is difluoromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, heptafluoropropyl or difluoro(phenyl)methyl.
n represents an integer of 0 or 1; ]
Isoxazole compound represented by or a salt thereof. 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole; 3-(2-fluoro-4-methyl -5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(heptafluoropropyl)isoxazole; 5-(difluoromethyl)-3-(2-fluoro-4-methyl-5- ((2,2,2-trifluoroethyl)thio)phenyl)isoxazole; 5-(chlorodifluoromethyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoro Ethyl)sulfinyl)phenyl)isoxazole; 5-(Difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole; 3-(2,4-dimethyl- 5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole; 3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5 -(trifluoromethyl)isoxazole; 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl) isoxazole; 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole; 3-(2-chloro- 4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole; 5-(difluoromethyl)-3-(2,4-dimethyl-5 -((2,2,2-trifluoroethyl)thio)phenyl)isoxazole; 5-(difluoromethyl)-3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl) sulfinyl)phenyl)isoxazole; 5-(chlorodifluoromethyl)-3-(2,4-dimethyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole; 5-(chlorodifluoro methyl)-3-(2,4-dimethyl-5-((2,2,2-tri fluoroethyl)sulfinyl)phenyl)isoxazole; 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoro(phenyl)methyl)iso Oxazole; 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoro(phenyl)methyl)isoxazole; 3-(2-chloro -4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoromethyl)isoxazole; and 3-(2-chloro-4-methyl-5-((2 , 2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoromethyl)isoxazole, or a salt thereof according to claim 1. 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole; 3-(2-fluoro-4-methyl -5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(heptafluoropropyl)isoxazole; 5-(difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl) -5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole; 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl )-5-(trifluoromethyl)isoxazole; 3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5-(trifluoromethyl)isoxazole; 3-(2-fluoro-4 -methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole; 3-(2-chloro-4-methyl-5-( (2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole; 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl) )sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole; 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoro methyl)isoxazole; and 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoromethyl)isoxazole The isoxazole compound or a salt thereof according to claim 1. 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole; 5-(chlorodifluoromethyl)-3- (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)isoxazole; 5-(difluoro(phenyl)methyl)-3-(2-fluoro-4-methyl) -5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole; 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl )-5-(trifluoromethyl)isoxazole; 3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5-(trifluoromethyl)isoxazole; 3-(2-fluoro-4 -methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole; 3-(2-chloro-4-methyl-5-( (2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole; 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl) )sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole; 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(difluoro methyl)isoxazole; and 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoromethyl)isoxazole The isoxazole compound or a salt thereof according to claim 1. 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole; 5-(difluoro(phenyl)methyl)- 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoxazole; 3-(2-chloro-4-methyl-5-((2,2 , 2-trifluoroethyl)sulfinyl)phenyl)-5-(trifluoromethyl)isoxazole; 3-(2-fluoro-4-methyl-5-(propylsulfinyl)phenyl)-5-(trifluoromethyl)iso Oxazole; 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-4-methyl-5-(trifluoromethyl)isoxazole; 3-(2 -chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-5-(chlorodifluoromethyl)isoxazole; 3-(2-chloro-4-methyl-5-( (2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(chlorodifluoromethyl)isoxazole; 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl) )thio)phenyl)-5-(difluoromethyl)isoxazole; and 3-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-5-(difluoro The isoxazole compound or salt thereof according to claim 1, which is selected from the group consisting of methyl)isoxazole. A pest control agent comprising the isoxazole compound or its salt according to any one of claims 1 to 5 as an active ingredient. Agricultural use containing the isoxazole compound or salt thereof according to any one of claims 1 to 5 for controlling pests, for acaricidal purposes, for ovicidal purposes, for nematicidal purposes, and for controlling mites for the control of nematodes, for use in the control of mites, for use in the control of eggs or ova, for use in the control of nematodes, pests, habitats of pests, or places where they are expected to inhabit to control pests; to mites, to mites or to places where mites are or are expected to live; to kill mites; to eggs or where eggs are expected to be laid; to kill eggs; , a composition for application to nematodes, nematode habitats or where nematode inhabitants are expected to kill nematodes .